Medicinal Plants of the Asia-Pacific - Drugs for the Future - C. Wiart (World, 2006) BBS

MEDICINAL PLANTS OF THE AISA-PACIFIC: DRUGS FOR THE FUTURE?

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MEDICINAL PLANTS OF THE AISA-PACIFIC: DRUGS FOR THE FUTURE?

CHRISTOPHE WIART University of Malaya, Malaysia

World Scientific NEW JERSEY • LONDON • SINGAPORE • BEIJING • SHANGHAI • HONG KONG • TAIPEI • CHENNAI

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British Library Cataloguing-in-Publication Data A catalogue record for this book is available from the British Library.

MEDICINAL PLANTS OF THE ASIA-PACIFIC Drugs for the Future? Copyright © 2006 by World Scientific Publishing Co. Pte. Ltd. All rights reserved. This book, or parts thereof, may not be reproduced in any form or by any means, electronic or mechanical, including photocopying, recording or any information storage and retrieval system now known or to be invented, without written permission from the Publisher.

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...Tum cynaeis erepit ab undis Insula, quae prisci signatur nominis usu Aurea, quod fulvo sol hic magis orbe rubescat Rufus Festus Avienus AD 370

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Preface

Looking globally, there is a considerable interest to find cure from nature. We all know that in some sense there are drugs awaiting discovery in nature and especially in medicinal plants. The question that grips us is, why ? Why are these drugs undiscovered in spite of enormous technical achievements. If the scientific techniques of pharmacological evaluations are so well mastered, it is natural to expect an increasing number of important drugs discovered from plants, thus improving human health drastically. Instead, we observe that cancers and microbial infections are still life threatening. This observation raises several questions: 1. What is the present rationale in terms of the research of drugs from plants? 2. Should we reconsider our strategies in assessing medicinal plants and opt for an alternative approach? 3. In regard to the pharmacological activities measured so far, why should these be circumjacent of plant species? 4. Do they exist above the level of the plant species, where subclasses and orders might experience macrolevel intrinsic content? 5. Are we targeting the correct groups of lead compounds? 6. Is ethnopharmacology really used as a tool to excavate drugs, or is it a mere transitory fashion? In other words, what role does ethnopharmacology really play in today’s high technological world of drug discovery? By constitutively interconnecting several aspects of phylogeny, taxonomy, ethnology, structure–activity relationship, molecular pharmacology and toxicology, I attempt to answer these questions from the first principles with a premier reference source for traditional medicine and the development of drugs from plants, especially from the medicinal plants of a region I had the opportunity to explore: Asia-Pacific. This may seem like an extraordinary project because the topics of botany, chemistry and pharmacology are individual and independent disciplines as its own. It is not clear that thumping them together will really help us crack them open. My burden is to argue that they need to be treated together, and to show, in a very concrete manner, how they do go hand-in-hand in opening the little door of scientific consciousness.

vii

viii

Preface

This book proposes a place for consciousness in ethnopharmacology, and to a more general sense, an alternative approach to the discovery of drugs from plants; an approach I would like to call phytopharmacology. The framework developed here is ambitious in its scope and detail. It ties experience with a theory of the botanical and ethnological foundations of plant bioactivities. Scholars should see it as an attempt to advance in the development of Mark J. Plotkin’s Medicine Quest: In Search of Nature’s Healing Secrets, by borrowing some inspiration from Cronquist’s system of taxonomy. General readers can simply see it as an attempt to explain the why of a medicinal property. Within the book, I often point to the lack of pharmacological and/or toxicological scientific evidences on specific plants or taxa. I believe this framework should at least cause some stirs in pharmacologists, by showing that most plants on the verge of extinction, remain yet to be assessed. No one should rest comfortably with any assumption that the present approach in drug discovery must lead to unreasonableness. At the next level of ambition, I hope to challenge the readers. Pharmacologist’s strongest support has so far been the widespread use of massive automated screenings to guarantee the discovery of lead compounds in an acceptable way. A first challenge that this book propose is by showing that the pharmacological profile of a given plant or taxa is understandable and therefore predictable, we need a more thoughtful and sensitive approach. Pharmacological activities make sense only against a detailed background theory of botanical and chemical causation. A second challenge is to see whether the ideas lead to fruitful avenues of research, or whether they lead to a dead end instead. The book presents a framework, providing a new perspective from which we could understand nature. At a third level, I hope to actually stimulate further research on the discovery of drugs from the medicinal plants of Asia-Pacific. To date, there is a lack of books on medicinal plants in Asia-Pacific, one of the richest region in terms of biodiversity as well as a rich source for traditional medicines. This book provides a very detailed ethnopharmacological accounting of over 400 plant species, enhanced by more than 300 original pictures, 400 chemical structures, voucher plants, pharmaceutical interest and thousands of bibliographic references. I have made the book as accessible and interesting as possible to the general public, even to those who have little or no specific training in biological sciences. My intention was not to pontify, but merely to create something where its importance lies beyond the details of its presentation. I consider this to be primarily a book of personal thoughts. Of all my hopes, my dearest is that Medicinal Plants of Asia–Pacific: Drugs for the Future? should provide inspiration to those looking for drugs from plants. In the space of ideas, I believe

Preface

ix

that this book acts as a pointer to the existence of originality, where readers could freely explore endlessly on their own. Christophe Wiart Pharm. D. Associate Professor of Pharmacognosy Department of Pharmacy University of Malaya 50603 Kuala Lumpur Malaysia

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Contents

Preface

vii

Foreword Farnsworth

xxxi

Foreword Etkin

xxxiii

Foreword Williamson

xxxv

Class MAGNOLIOPSIDA Cronquist, Takhtajan & Zimmermann 1966, the Dicotyledons

1

I. Subclass MAGNOLIIDAE Takhtajan 1966

1

A. Order MAGNOLIALES Bromhead 1838

2

1. Family HIMANTANDRACEAE Diels 1917 nom. conserv., the Himantandra Family Galbulimima belgraveana (F. Muell.) Sprague . . . . . . . . 2. Family ANNONACEAE A. L. de Jussieu 1789 nom. conserv., the Custard-apple Family Anaxagorea javanica Bl. . . . . . . . . . . . . . . . . . . . . Annona muricata L. . . . . . . . . . . . . . . . . . . . . . . . Artabotrys suaveolens Bl. . . . . . . . . . . . . . . . . . . . . Cananga odorata (Lamk.) Hook. f. & Thoms. . . . . . . . . Cyathostemma argenteum (Bl.) J. Sinclair . . . . . . . . . . Desmos chinensis Lour. . . . . . . . . . . . . . . . . . . . . . Fissistigma species . . . . . . . . . . . . . . . . . . . . . . . Goniothalamus macrophyllus (Bl.) Hook. f. & Thoms. . . . Mitrella kentii (Bl.) Miq. . . . . . . . . . . . . . . . . . . . . . Orophea polycarpa A. DC. . . . . . . . . . . . . . . . . . . . Polyalthia cauliflora Hook. f. & Thoms. var. beccarii (King) J. Sinclair . . . . . . . . . . . . . . . . . . . . . . . . . . . . xi

2 2 4 5 7 9 11 13 14 15 17 19 20 21

xii

Contents

Pyramidanthe prismatica J. Sinclair (Hook. f. & Thoms.) . . . . . . . . . . . . . . . . . . . . . . Uvaria grandiflora Roxb. . . . . . . . . . . . . . . . . . . . .

23 24

3. Family MYRISTICACEAE R. Brown 1810 nom. conserv., the Nutmeg Family Horsfieldia irya (Gaertn.) Warb. . . . . . . . . . . . . . . . Knema globularia (Lamk.) Warb. . . . . . . . . . . . . . . . Myristica iners Bl. . . . . . . . . . . . . . . . . . . . . . . . .

27 28 29 30

B. Order LAURALES Lindley 1833

31

1. Family LAURACEAE A. L. de Jussieu 1789 nom. conserv., the Laurel Family Cassytha filiformis L. . . . . . . . . . . . . . . . . . . . . . . . Cinnamomum iners Reinw. ex Bl. . . . . . . . . . . . . . . . Litsea glutinosa (Lour.) C.BV. Robinson . . . . . . . . . . . C. Order PIPERALES Lindley 1833

31 32 34 36 37

1. Family CHLORANTHACEAE R. Brown ex Lindley 1821 nom. conserv., the Chloranthus Family Chloranthus eliator R. Br. ex Link . . . . . . . . . . . . . . . Sarcandra glabra (Thunb.) Nak. . . . . . . . . . . . . . . . .

37 38 39

2. Family PIPERACEAE C. A. Agardh 1825 nom conserv., the Pepper Family Piper cubeba L. f . . . . . . . . . . . . . . . . . . . . . . . . . Peperomia pellucida (L.) HBK. . . . . . . . . . . . . . . . . .

40 41 43

D. Order ARISTOLOCHIALES Lindley 1833 1. Family ARISTOLOCHIACEAE A. conserv., the Birthwort Family Apama corymbosa (Griff.) Willd. . Apama tomentosa (Bl.) O. Ktze. . Aristolochia indica L. . . . . . . . . Aristolochia tagala Cham. . . . . Asarum sieboldii Miq. . . . . . . . Thottea dependens Klotzsch . . .

44

L. de Jussieu 1789 nom. . . . . . .

. . . . . .

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. . . . . .

. . . . . .

E. Order RANUNCULALES Lindley 1833 1. Family RANUNCULACEAE A.L. de Jussieu 1789 nom. conserv., the Buttercup Family Coptis japonica (Thunb.) Mak. . . . . . . . . . . . . . . . . . Ranunculus sceleratus L. . . . . . . . . . . . . . . . . . . . .

44 45 46 46 49 50 51 52 52 54 56

Contents

xiii

2. Family BERBERIDACEAE A. L. de Jussieu 1789 nom. conserv., the Barberry Family Berberis thunbergii DC. . . . . . . . . . . . . . . . . . . . . . Caulophyllum robustum Maxim. . . . . . . . . . . . . . . . .

57 59 60

3. Family LARDIZABALACEAE Decaisne 1838 nom. conserv., the Lardizabala Family Akebia quinata (Thunb.) Decne. . . . . . . . . . . . . . . . .

62 62

4. Family MENISPERMACEAE A. L. de Jussieu 1789 nom. conserv., the Moonseed Family. Fibraurea chloroleuca Miers . . . . . . . . . . . . . . . . . . Pericampylus glaucus (Lamk.) Merr. . . . . . . . . . . . . .

63 65 66

F. Order PAPAVERALES Cronquist 1981

67

1. Family PAPAVERACEAE A. L. de Jussieu 1789 nom. conserv., the Poppy Family Argemone mexicana L. . . . . . . . . . . . . . . . . . . . . . Chelidonium majus L. . . . . . . . . . . . . . . . . . . . . . .

68 69 70

2. Family FUMARIACEAE A. P. de Candolle 1821 nom. conserv., the Fumitory Family Corydalis incisa (Thunb.) Pers. . . . . . . . . . . . . . . . .

72 74

II. Subclass HAMAMELIDAE Takhtajan 1966 A. Order URTICALES Lindley 1833 1. Family CANNABACEAE Endlicher 1837 nom. conserv., the Hemp Family Cannabis sativa L. . . . . . . . . . . . . . . . . . . . . . . . . Humulus scandens (Lour.) Merr. . . . . . . . . . . . . . . . . 2. Family MORACEAE Link 1831 nom. conserv., the Mulberry Family Antiaris toxicaria Lesch. . . . . . . . . . . . . . . . . . . . . . Artocarpus heterophyllus Lamk. . . . . . . . . . . . . . . . . Parartocarpus venenosus (Zoll. & Mor.) Becc. ssp. forbesii (King) Jarret . . . . . . . . . . . . . . . . . . . . . B. Order FAGALES Engler 1892 1. Family FAGACEAE Dumortier 1829 nom. conserv., the Beech Family Castanea crenata Sieb. & Zucc. . . . . . . . . . . . . . . . . Castanopsis cuspidata (Thunb.) Schottky . . . . . . . . . .

75 75 75 76 79 80 81 83 85 86 86 86 88

xiv

Contents

Lithocarpus elegans (Bl.) Hatus. ex Soepadmo . . . . . . . Quercus acutissima Carruthers . . . . . . . . . . . . . . . . III. Subclass CARYOPHYLLIDAE Takhtajan 1966

89 90 91

A. Order CARYOPHYLLALES Bentham & Hooker 1862

91

1. Family AIZOACEAE Rudolphi 1830 nom. conserv., the Fig — marigold Family Tetragonia tetragonioides (Pallas) O. Ktze. . . . . . . . . . . Trianthema portulacastrum L. . . . . . . . . . . . . . . . . .

91 92 93

2. Family CACTACEAE A. L. de Jussieu 1789 nom. conserv., the Cactus Family Opuntia dillenii (Ker — Gawl.) Haworth . . . . . . . . . . . Pereskia bleo DC . . . . . . . . . . . . . . . . . . . . . . . . .

95 96 98

3. Family CHENOPODIACEAE Ventenat 1799 nom. conserv., the Goosefoot Family 99 Chenopodium album L. . . . . . . . . . . . . . . . . . . . . . 100 Kochia scoparia (L.) Schrader . . . . . . . . . . . . . . . . . 101 4. Family AMARANTHACEAE A. L. de Jussieu 1789 nom. conserv., the Amaranth Family Achyranthes aspera L. . . . . . . . . . . . . . . . . . . . . Achyranthes bidentata Bl. . . . . . . . . . . . . . . . . . . . Alternanthera sessilis (L.) R. Br. . . . . . . . . . . . . . . Aerva lanata (L.) Juss. . . . . . . . . . . . . . . . . . . . . Amaranthus spinosus L. . . . . . . . . . . . . . . . . . . . Celosia argentea L. . . . . . . . . . . . . . . . . . . . . . . Cyathula prostrata (L.) Bl. . . . . . . . . . . . . . . . . . . . Deeringia amaranthoides (Lamk.) Merr. . . . . . . . . . . Gomphrena globosa L. . . . . . . . . . . . . . . . . . . . .

. . . . . . . . .

103 103 107 108 110 112 113 116 117 118

5. Family MOLLUGINACEAE Hutchinson 1926, nom. conserv., the Carpet - weed Family 119 Mollugo pentaphylla L. . . . . . . . . . . . . . . . . . . . . . 120 6. Family CARYOPHYLLACEAE A. L. de Jussieu 1789 nom. conserv., the Pink Family Drymaria cordata Willd. . . . . . . . . . . . . . . . . . . . . . Polycarpaea corymbosa Lamk. . . . . . . . . . . . . . . . . Saponaria vaccaria L. . . . . . . . . . . . . . . . . . . . . . . Silene aprica Turcz. . . . . . . . . . . . . . . . . . . . . . . .

121 122 124 125 126

Contents

B. Order POLYGONALES Lindley 1833

xv

127

1. Family POLYGONACEAE A. L. de Jussieu 1789 nom. conserv., the Buckwheat Family Polygonum barbatum L. . . . . . . . . . . . . . . . . . . . . . Polygonum chinense L. . . . . . . . . . . . . . . . . . . . . .

127 128 130

IV. Subclass DILLENIIDAE Takhtajan 1966

132

A. Order DILLENIALES Hutchinson 1926

132

1. Family DILLENIACEAE Salisbury 1807 nom. conserv., the Dillenia family Acrotrema costatum Jack . . . . . . . . . . . . . . . . . . . . Dillenia excelsa (Jack) Gilg . . . . . . . . . . . . . . . . . . . Dillenia indica L. . . . . . . . . . . . . . . . . . . . . . . . . . Tetracera indica (Houtt. ex Christm. & Panz.) Merr. . . . . . B. Order THEALES Lindley 1833

132 133 134 135 136 138

1. Family DIPTEROCARPACEAE Blume 1825 nom. conserv., the Meranti Family Dipterocarpus alatus Roxb. . . . . . . . . . . . . . . . . . . . Dipterocarpus intricatus Dyer . . . . . . . . . . . . . . . . . Dipterocarpus obtusifolius Miq. . . . . . . . . . . . . . . . . Dryobalanops aromatica Gaertn. . . . . . . . . . . . . . . . Hopea odorata Roxb. . . . . . . . . . . . . . . . . . . . . . . Shorea sumatrana (van. Sl. Ex Foxw) Sym. . . . . . . . . .

138 139 140 141 142 144 145

2. Family THEACEAE D.Don 1825 nom. conserv., the Tea Family Camellia sinensis (L.) O. Ktze. . . . . . . . . . . . . . . . . .

146 147

3. Family CLUSIACEAE Lindley 1826 nom. conserv., the Mangosteen Family Calophyllum inophyllum L. . . . . . . . . . . . . . . . . . Cratoxylum cochinchinense (Lour.) Bl. . . . . . . . . . . Garcinia mangostana L. . . . . . . . . . . . . . . . . . . . Hypericum japonicum Thunb. . . . . . . . . . . . . . . . Mesua ferrea L. . . . . . . . . . . . . . . . . . . . . . . . .

149 150 152 154 156 158

C. Order MALVALES Lindley 1833

. . . . .

. . . . .

160

1. Family ELAEOCARPACEAE A. P. de Candolle 1824 nom. conserv., the Elaeocarpus Family 160 Elaeocarpus grandiflorus Smith . . . . . . . . . . . . . . . . 161

xvi

Contents

Elaeocarpus sphaericus (Gaertn.) K. Sch. . . . . . . . . . . Elaeocarpus stipularis Bl. . . . . . . . . . . . . . . . . . . . .

162 163

2. Family BOMBACACEAE Kunth 1822 nom. conserv., the Kapok-tree Family Durio zibethinus Murr. . . . . . . . . . . . . . . . . . . . . . .

164 164

D. Order LECYTHIDALES Cronquist 1957

166

1. Family LECYTHIDACEAE Poiteau 1825 nom. conserv., the Brazil-nut Family 166 Barringtonia acutangula (L.) Gaertn. . . . . . . . . . . . . . 167 E. Order NEPENTHALES Lindley 1833

168

1. Family NEPENTHACEAE Dumortier 1829 nom. conserv., the East Indian Pitcher-plant Family. 169 Nepenthes ampullaria Jack . . . . . . . . . . . . . . . . . . 170 2. Family DROSERACEAE Salisbury 1808 nom. conserv., the Sundew Family. 170 Drosera burmannii Vahl . . . . . . . . . . . . . . . . . . . . 171 Drosera indica L. . . . . . . . . . . . . . . . . . . . . . . . . . 173 F. Order VIOLALES Lindley 1833

173

1. Family FLACOURTIACEAE A. P. de Candolle 1824 nom. conserv., the Flacourtia Family Casearia grewiaefolia Vent. . . . . . . . . . . . . . . . . . . . Flacourtia rukam Zoll. & Mor. . . . . . . . . . . . . . . . . . . Hydnocarpus species . . . . . . . . . . . . . . . . . . . . . . Pangium edule Reinw. . . . . . . . . . . . . . . . . . . . . . . Xylosma congesta (Lour.) Merr. . . . . . . . . . . . . . . . .

174 174 175 176 177 178

2. Family BIXACEAE Link. 1831 nom. conserv., the Lipstick-tree Family Bixa orellana L. . . . . . . . . . . . . . . . . . . . . . . . . . .

179 179

3. Family ANCISTROCLADACEAE Walpers 1851 nom. conserv., the Ancistrocladus Family Ancistrocladus tectorius (Lour.) Merr. . . . . . . . . . . . . .

181 181

4. Family CARICACEAE Dumortier 1829, nom. conserv., the Papaya Family Carica papaya L. . . . . . . . . . . . . . . . . . . . . . . . . .

183 184

5. Family CUCURBITACEAE A. L. de Jussieu 1789 nom. conserv., the Cucumber family

186

Contents

Benincasa hispida (Thunb.) Cogn. . . . . . . Citrullus lanatus (Thunb.) Matsum. & Nak. . . Lagenaria siceraria (Mol.) Standl. . . . . . . . Luffa acutangula Roxb. . . . . . . . . . . . . . Momordica charantia L. . . . . . . . . . . . . . Momordica cochinchinensis (Lour.) Spreng. . Trichosanthes kirilowii Maxim. . . . . . . . . .

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xvii

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188 190 191 193 194 198 200

6. Family DATISCACEAE Lindley 1830 nom. conserv., the Datisca Family Octomeles sumatrana Miq. . . . . . . . . . . . . . . . . . . .

201 202

7. Family BEGONIACEAE C. A. Agardh 1825, nom. conserv., the Begonia Family Begonia species . . . . . . . . . . . . . . . . . . . . . . . . .

202 203

G. Order CAPPARALES Hutchinson 1926

205

1. Family CAPPARACEAE A. L. de Jussieu 1789 nom. conserv., the Caper Family Cleome gynandra L. . . . . . . . . . . . . . . . . . . . . Cleome viscosa L. . . . . . . . . . . . . . . . . . . . . . Capparis zeylanica L. . . . . . . . . . . . . . . . . . . . Crateva magna (Lour.) DC. . . . . . . . . . . . . . . . . Stixis scortechinii (King) Jacobs . . . . . . . . . . . . .

. . . . .

2. Family BRASSICACEAE G. T. Burnett the Mustard family Brassica juncea (L.) Cosson . . . . . . Capsella bursa-pastoris (L.) Medic. . . Cardamine hirsuta L. . . . . . . . . . . Nasturtium indicum DC. . . . . . . . . . Nasturtium officinale R. Br. . . . . . . .

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205 206 208 210 211 212

1835 nom. conserv., . . . . .

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H. Order ERICALES Lindley 1833

213 214 215 217 218 219 220

1. Family EPACRIDACEAE R. Brown 1810 nom. conserv., the Epacris Family 220 Leucopogon Malayanus Jack . . . . . . . . . . . . . . . . . 221 2. Family ERICACEAE A. L. de Jussieu 1789 nom. the Heath Family Lyonia ovalifolia (Wall.) Drude . . . . . . . . . . . . Rhododendron moulmainense Hook . . . . . . . . Vaccinium vitis-idaea L. . . . . . . . . . . . . . . . .

conserv., . . . . . . . . . . . . . . .

222 223 224 225

xviii

Contents

I. Order EBENALES Engler 1892

227

1. Family EBENACEAE Gurke in Engler & Prantl 1891 nom. conserv., the Ebony Family Diospyros argentea Griff. . . . . . . . . . . . . . . . . . . . . Diospyros kaki L. f. . . . . . . . . . . . . . . . . . . . . . . . . Diospyros wallichii K. & G. ex Williams . . . . . . . . . . . .

227 228 230 231

2. Family STYRACACEAE Dumortier 1829 nom. conserv., the Storax Family 232 Styrax benzoin Dryand. . . . . . . . . . . . . . . . . . . . . . 233 J. Order PRIMULALES Lindley 1833 1. Family MYRSINACEAE R. Brown 1810 Myrsine family Ardisia crispa A. DC. . . . . . . . . . . . . Embelia ribes Burm. f. . . . . . . . . . . . Labisia pumila ( BI.) Benth. & Hook. . .

234 nom. conserv., the . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

234 235 237 239

V. Subclass ROSIDAE Takhtajan 1966

240

A. Order ROSALES Lindley 1833

240

1. FAMILY CONNARACEAE R. Brown in Tuckey 1818 nom. conserv., the Connarus Family Agelaea trinervis (Llanos) Merr. . . . . . . . . . . . . Cnestis palala (Lour.) Merr. . . . . . . . . . . . . . . . Connarus monocarpus L. . . . . . . . . . . . . . . . . Connarus semidecandrus Jack . . . . . . . . . . . . Rourea minor (Gaertn.) Leenh. . . . . . . . . . . . . Roureopsis emarginata (Jack) Merr. . . . . . . . . .

. . . . . .

240 241 242 243 244 245 246

2. Family CUNONIACEAE R. Brown. in Flinders 1814 nom. conserv., the Cunonia Family Weinmannia blumei Planch. . . . . . . . . . . . . . . . . . .

247 248

3. Family PITTOSPORACEAE R. Brown in Flinders 1814 nom conserv., the Pittosporum Family Pittosporum tobira (Thunb.) Ait. . . . . . . . . . . . . . . . .

249 250

4. Family CRASSULACEAE A. P. de Candolle in Lamarck & de Candolle 1805 nom. conserv., the Stonecrop Family Kalanchoe laciniata (L.) DC . . . . . . . . . . . . . . . . . . Kalanchoe pinnata (Lamk.) Pers . . . . . . . . . . . . . . .

251 251 252

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Contents

xix

Sedum alfredi Hance . . . . . . . . . . . . . . . . . . . . . . Sedum bulbiferum Mak. . . . . . . . . . . . . . . . . . . . . .

254 255

B. Order FABALES Bromhead 1838 1. Family MIMOSACEAE R. Brown in Flinders 1814 nom. conserv., the Mimosa Family Acacia farnesiana (L.) Willd . . . . . . . . . . . . . Adenanthera pavonina L. . . . . . . . . . . . . . . . Entada phaseoloides (L.) Merr. . . . . . . . . . . . Leucaena leucocephala (Lamk.) de Wit . . . . . . Mimosa pudica L. . . . . . . . . . . . . . . . . . . . Parkia speciosa Hassk . . . . . . . . . . . . . . . .

256

. . . . . .

. . . . . .

257 257 259 260 261 264 265

2. Family CAESALPINIACEAE R. Brown in Flinders 1814 nom. conserv., the Caesalpinia Family Bauhinia purpurea L. . . . . . . . . . . . . . . . . . . . . . Caesalpinia bonduc (L.) Roxb. . . . . . . . . . . . . . . . . Caesalpinia sappan L. . . . . . . . . . . . . . . . . . . . . . Cassia alata L. . . . . . . . . . . . . . . . . . . . . . . . . . Cassia tora L. . . . . . . . . . . . . . . . . . . . . . . . . . . Tamarindus indicus L. . . . . . . . . . . . . . . . . . . . . .

. . . . . .

266 268 269 271 272 274 276

. . . . . .

. . . . . .

. . . . . .

3. Family FABACEAE Lindley 1836 nom. conserv., the Pea or Bean Family Abrus precatorius L. . . . . . . . . . . . . . . . . . . . . . . . Alysicarpus vaginalis (L.) DC. . . . . . . . . . . . . . . . . . Erythrina subumbrans (Hassk.) Merr. . . . . . . . . . . . . . Indigofera tinctoria L. . . . . . . . . . . . . . . . . . . . . . . Pongamia pinnata (L.) Merr. . . . . . . . . . . . . . . . . . . C. Order PROTEALES Lindley 1833 1. Family ELAEAGNACEAE A. L. de Jussieu 1789 nom. conserv., the Oleaster Family Elaeagnus latifolia L. . . . . . . . . . . . . . . . . . . . . . . . D. Order MYRTALES Lindley 1833 1. Family LYTHRACEAE Jaume St.-Hilaire 1805 nom. conserv., the Loosestrife Family Ammannia baccifera L. . . . . . . . . . . . . . . . . . . . . . Lagerstroemia subcostata Koehne . . . . . . . . . . . . . . Woodfordia fruticosa (L.) Kurz . . . . . . . . . . . . . . . . .

277 279 280 281 283 284 285 285 286 287 287 288 288 290

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Contents

2. Family ONAGRACEAE A.L. de Jussieu 1798 nom conserv., the Evening Primrose Family 291 Ludwigia hyssopifolia (D. Don) Exell . . . . . . . . . . . . . 292 3. Family MELASTOMATACEAE A. L. de Jussieu 1789, nom conserv., the Melastoma Family Melastoma candidum D. Don . . . . . . . . . . . . . . . . . Memecylon edule Roxb. . . . . . . . . . . . . . . . . . . . . Phyllagathis rotundifolia (Jack.) Bl. . . . . . . . . . . . . . . Sonerila begoniaefolia Ridl. . . . . . . . . . . . . . . . . . .

293 294 296 296 297

4. Family COMBRETACEAE R. Brown 1810 nom. conserv., the Indian Almond Family 298 Quisqualis indica L. . . . . . . . . . . . . . . . . . . . . . . . 298 Terminalia chebula Retz. . . . . . . . . . . . . . . . . . . . . 299 E. Order CORNALES Lindley 1833

301

1. Family ALANGIACEAE A.P. de Candolle 1828 nom. conserv., the Alangium Family Alangium chinense (Lour.) Harms . . . . . . . . . . . . . . .

301 302

2. Family CORNACEAE Dumortier 1829 nom. conserv., the Dogwood Family Aralidium pinnatifidum Miq. . . . . . . . . . . . . . . . . . . .

303 304

F. Order SANTALALES Lindley 1833

305

1. Family OLACACEAE Mirbel ex A. P. de Candolle 1824 nom. conserv., the Olax Family 305 Olax scandens Roxb. . . . . . . . . . . . . . . . . . . . . . . 306 Scorodocarpus borneensis Becc. . . . . . . . . . . . . . . . 307 2. Family LORANTHACEAE A. L. de Jussieu 1808, nom conserv., the Mistletoe Family Macrosolen cochichinensis (Lour.) van Tieghem . . . . . . Dendrophthoe pentandra (L.) Miq. . . . . . . . . . . . . . . G. Order RAFFLESIALES Kerner 1891

309 309 310 311

1. Family RAFFLESIACEAE Dumortier 1829 nom. conserv., the Rafflesia Family 311 Rafflesia hasseltii Suring . . . . . . . . . . . . . . . . . . . . 311 H. Order CELASTRALES Wettstein 1907 1. Family CELASTRACEAE R. Brown in Flinders 1814 nom. conserv., the Bittersweet Family

312 312

Contents

Celastrus monospermoides Loes. . . . . . . Celastrus paniculata Willd. . . . . . . . . . . Euonymus alatus (Thunb.) Sieb. . . . . . . . Gymnosporia spinosa (Blco.) Merr. & Rolfe

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. . . .

. . . .

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. . . .

xxi

. . . .

314 315 317 319

2. Family HIPPOCRATEACEAE A. L. de Jussieu 1811 nom. conserv., the Hippocratea Family Salacia grandiflora Kurz . . . . . . . . . . . . . . . . . . . . .

320 321

3. Family AQUIFOLIACEAE Bartling 1830 nom. conserv., the Holly Family Ilex pubescens Hook. & Arn. . . . . . . . . . . . . . . . . . .

322 323

4. Family ICACINACEAE Miers 1851 nom. conserv., the Icacina Family Gomphandra quadrifida (Bl.) Sleum. var. angustifolia (King) Sleum. . . . . . . . . . . . . . . . . . . . . . . . . . . 5. Family DICHAPETALACEAE Baillon in Martius 1886, nom. conserv., the Dichapetalum Family Dichapetalum griffithii (Hook. f.) Engl. . . . . . . . . . . . . I. Order EUPHORBIALES Lindley 1833 1. Family EUPHORBIACEAE A. L. de Jussieu 1789 nom. conserv., the Spurge Family Acalypha indica L. . . . . . . . . . . . . . . . . . . . Acalypha siamensis Oliv. ex Gage . . . . . . . . . Acalypha wilkesiana M. A. . . . . . . . . . . . . . . Alchornea villosa (Benth.) Muell.-Arg. . . . . . . . Aleurites moluccana (L.) Willd. . . . . . . . . . . . . Aporosa arborea Muell.-Arg. . . . . . . . . . . . . . Breynia fruticosa (L.) Hook. f. . . . . . . . . . . . . Breynia reclinata (Muell. Arg.) Hook. f. . . . . . . . Bridelia penangiana Hook. f. . . . . . . . . . . . . . Bridelia stipularis (L.) Bl. . . . . . . . . . . . . . . . Cleidion spiciflorum (Burm. f.) Merr. . . . . . . . . . Codiaeum variegatum (L.) Bl. . . . . . . . . . . . . Croton argyratus Bl. . . . . . . . . . . . . . . . . . . Croton cascarilloides Raeusch. . . . . . . . . . . . Croton tiglium L. . . . . . . . . . . . . . . . . . . . . Euphorbia antiquorum L. . . . . . . . . . . . . . . . Euphorbia hirta L. . . . . . . . . . . . . . . . . . . . Excoecaria agallocha L. . . . . . . . . . . . . . . . . Glochidion littorale Bl. . . . . . . . . . . . . . . . . .

325 326 327 327 329

. . . . . . . . . . . . . . . . . . .

. . . . . . . . . . . . . . . . . . .

. . . . . . . . . . . . . . . . . . .

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. . . . . . . . . . . . . . . . . . .

329 330 332 333 335 336 338 339 340 341 342 344 345 346 347 348 349 350 352 354

xxii

Contents

Glochidion rubrum Bl. . . . . . . . . . . . . . . . . . . Homonoia riparia Lour. . . . . . . . . . . . . . . . . . Jatropha curcas L. . . . . . . . . . . . . . . . . . . . . Macaranga denticulata (Bl.) Muell.-Arg. . . . . . . . Mallotus philippensis (Lamk.) Muell. Arg. . . . . . . Melanolepis multiglandulosa (Bl.) Reichb. F. & Zoll. Phyllanthus emblica L. . . . . . . . . . . . . . . . . . Phyllanthus niruri L. . . . . . . . . . . . . . . . . . . . Ricinus communis L. . . . . . . . . . . . . . . . . . . . Sapium sebiferum (L.) Roxb. . . . . . . . . . . . . . . Sauropus androgynus (L.) Merr. . . . . . . . . . . . .

. . . . . . . . . . .

. . . . . . . . . . .

. . . . . . . . . . .

. . . . . . . . . . .

J. Order LINALES Cronquist 1957

355 356 357 359 361 363 364 366 368 370 371 372

1. Family IXONANTHACEAE Exell & Mendo¸ca 1951 nom. conserv., the Ixonanthes Family Ixonanthes icosandra Jack . . . . . . . . . . . . . . . . . . . K. Order POLYGALALES Bentham & Hooker 1862

372 373 374

1. Family MALPIGHIACEAE A. L. de Jussieu 1789 nom. conserv., the Barbados cherry Family Hiptage benghalensis Kurz . . . . . . . . . . . . . . . . . . .

374 375

2. Family POLYGALACEAE R. Brown in Flinders 1814 nom. conserv., the Milkwort Family Epirixanthes elongata Bl. . . . . . . . . . . . . . . . . . . . . Polygala brachystachya Bl. . . . . . . . . . . . . . . . . . . . Salomonia cantoniensis Lour. . . . . . . . . . . . . . . . . .

377 378 378 379

L. Order SAPINDALES Bentham & Hooker 1862

379

1. Family BURSERACEAE Kunth 1824 nom. conserv., the Frankincense Family Canarium littorale Bl. . . . . . . . . . . . . . . . . . . . . . .

380 381

2. Family ANACARDIACEAE Lindley 1830 nom. conserv., the Sumac Family Anacardium occidentale L. . . . . . . . . . . . . . . . . . . Campnosperma brevipetiolata Volk. . . . . . . . . . . . . Cotinus coggygria Scop. . . . . . . . . . . . . . . . . . . . Mangifera foetida Lour. . . . . . . . . . . . . . . . . . . . . Mangifera indica L. . . . . . . . . . . . . . . . . . . . . . . .

382 383 385 386 388 389

3. Family SIMAROUBACEAE A. P. de Candolle 1811 nom. conserv., the Quassia Family

. . . . .

390

Contents

Brucea javanica (L.) Merr. . . . . Eurycoma longifolia Jack . . . . . Harrisonia perforata (Blco.) Merr. Picrasma javanica Bl. . . . . . . .

. . . .

. . . .

. . . .

. . . .

. . . .

. . . .

. . . .

. . . .

. . . .

. . . .

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. . . .

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xxiii

. . . .

392 394 396 397

4. Family MELIACEAE A. L. DE Jussieu 1789 nom. conserv., the Mahogany Family 398 Swietenia mahogani (L.) Jacq. . . . . . . . . . . . . . . . . . 400 5. Family RUTACEAE A. L. de Jussieu 1789 nom. conserv., the Rue Family Acronychia laurifolia Bl. . . . . . . . . . . . . . . . . . . . . . Atalantia monophylla DC. . . . . . . . . . . . . . . . . . . . . Citrus grandis (L.) Osbeck . . . . . . . . . . . . . . . . . . . Clausena excavata Burm. f. . . . . . . . . . . . . . . . . . . Euodia latifolia DC. . . . . . . . . . . . . . . . . . . . . . . . . Micromelum hirsutum Oliv. . . . . . . . . . . . . . . . . . . . Murraya paniculata (L.) Jack . . . . . . . . . . . . . . . . . . Paramignya scandens (Griff.) Craib. var. ridleyi . . . . . . . Zanthoxylum nitidum (Roxb.) DC. . . . . . . . . . . . . . . . M. Order GERANIALES Lindley 1833

401 403 405 406 408 410 411 412 414 416 418

1. Family GERANIACEAE A. L. de Jussieu 1789 nom. conserv., the Geranium Family 418 Geranium nepalense Sweet . . . . . . . . . . . . . . . . . . 419 2. Family BALSAMINACEAE A. Richard 1822 nom. conserv., the Touch-me-not Family 421 Impatiens balsamina L. . . . . . . . . . . . . . . . . . . . . . 422 N. Order APIALES Nakai 1930 1. Family ARALIACEAE A. L. de Jussieu 1789 nom. conserv., the Ginseng Family Panax ginseng C. A. Meyer . . . . . . . . . . . . . . . . . . . Hedera rhombea (Miq.) Bean . . . . . . . . . . . . . . . . . Polyscias scutellaria (Burm. f) Fosberg . . . . . . . . . . . . Schefflera elliptica (Bl.) Harms . . . . . . . . . . . . . . . . . Schefflera octophylla (Lour.) Harms . . . . . . . . . . . . . VI. Subclass ASTERIDAE Takhtajan 1966 A. Order GENTIANALES Lindley 1833 1. Family LOGANIACEAE Martius 1827 nom. conserv., the Logania Family

424 424 425 429 430 432 432 434 434 435

xxiv

Contents

Fagraea fragrans Roxb. . . . . . . . . . . . . . . . . . . . . . Strychnos nux-vomica L. . . . . . . . . . . . . . . . . . . . .

435 436

2. Family GENTIANACEAE A. L. de Jussieu 1789 nom. conserv., the Gentian Family Swertia chirayita (Roxb.) Lyons . . . . . . . . . . . . . . . .

438 439

3. Family APOCYNACEAE A. L. de Jussieu 1789 nom. conserv., the Dogbane Family Aganosma marginata (Roxb.) G. Don . . . . . . . . . Allamanda cathartica L. . . . . . . . . . . . . . . . . . . Alyxia stellata (Forst.) Roem. et Schult. . . . . . . . . Alstonia scholaris (L.) R. Br. . . . . . . . . . . . . . . . Catharanthus roseus (L.) G. Don . . . . . . . . . . . . Cerbera odollam Gaertn. . . . . . . . . . . . . . . . . . Chonemorpha fragrans (Moon) Alston . . . . . . . . . Holarrhena antidysenterica (Roxb.) Wall. . . . . . . . Hunteria zeylanica (Retz.) Gardn. & Thw. . . . . . . . Kopsia fruticosa (Ker.) DC. . . . . . . . . . . . . . . . . Leuconotis eugeniifolius A. DC. . . . . . . . . . . . . . Nerium oleander L. . . . . . . . . . . . . . . . . . . . . Ochrosia oppositifolia (Lam.) K. Schum. . . . . . . . . Parameria laevigata (Juss.) Moldenke . . . . . . . . . Plumieria rubra L. sensu lato . . . . . . . . . . . . . . . Pottsia laxiflora (Bl.) O. Ktze. . . . . . . . . . . . . . . . Rauvolfia serpentina Benth. . . . . . . . . . . . . . . . Rauvolfia verticillata (Lour.) Baillon . . . . . . . . . . . Strophanthus caudatus (Burm. f) Kurz. . . . . . . . . . Tabernaemontana divaricata (L.) Burk. . . . . . . . . . Thevetia peruviana (Pers.) K. Schum. . . . . . . . . . Trachelospermum jasminoides (Lindl.) Lem. . . . . .

441 443 444 446 447 450 452 453 454 456 458 459 460 462 463 465 467 468 470 471 472 475 476

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. . . . . . . . . . . . . . . . . . . . . .

. . . . . . . . . . . . . . . . . . . . . .

4. Family ASCLEPIADACEAE R. Brown 1810 nom. conserv., the Milkweed Family Asclepias curassavica L. . . . . . . . . . . . . . . . . . . . . Calotropis gigantea (Willd.) Dry. ex WT. Ait . . . . . . . . . Cynanchum caudatum (Miq.) Maxim. . . . . . . . . . . . . . Dischidia rafflesiana Wall. . . . . . . . . . . . . . . . . . . . . Marsdenia tinctoria (Roxb.) R. Br. . . . . . . . . . . . . . . . Metaplexis japonica (Thunb.) Mak. . . . . . . . . . . . . . . Oxystelma esculentum (L. f.) R. Br. . . . . . . . . . . . . . . Sarcolobus globulus Wall. . . . . . . . . . . . . . . . . . . . Tylophora tenuis Bl. . . . . . . . . . . . . . . . . . . . . . . .

478 479 480 482 484 485 486 487 488 489

Contents

xxv

B. Order SOLANALES Lindley 1833

492

1. Family SOLANACEAE A. L. de Jussieu 1789 nom. Conserv., the Potato Family Datura stramonium L. . . . . . . . . . . . . . . . . . . . . . . Physalis angulata L. . . . . . . . . . . . . . . . . . . . . . . . Solanum torvum Sw. . . . . . . . . . . . . . . . . . . . . . . .

492 493 495 497

2. Family CONVOLVULACEAE A. L. de Jussieu 1789 nom. conserv., the Morning - glory Family Argyreia mollis (Burm. f.) Choisy . . . . . . . . . . . . . . Erycibe malaccensis C. B. Clarke . . . . . . . . . . . . . . Erycibe rheedii Bl. . . . . . . . . . . . . . . . . . . . . . . . Evolvulus alsinoides L. . . . . . . . . . . . . . . . . . . . . Ipomoea aquatica Forssk. . . . . . . . . . . . . . . . . . . Ipomoea cairica (L.) Sweet . . . . . . . . . . . . . . . . . . Ipomoea pes - caprae (L.) R. Br. . . . . . . . . . . . . . . .

499 500 501 502 503 504 505 507

. . . . . . .

C. Order LAMIALES Bromhead 1838

509

1. Family BORAGINACEAE A. L. de Jussieu 1789 nom. conserv., the Borage Family Carmona microphylla (Lamk.) Don . . . . . . . . . . . . . . Cordia dichotoma Forst. f. . . . . . . . . . . . . . . . . . . . Heliotropium indicum L. . . . . . . . . . . . . . . . . . . . . .

509 511 512 515

2. Family VERBENACEAE Jaume St. - Hilaire 1805 nom. conserv., the Verbena Family Vitex negundo L. . . . . . . . . . . . . . . . . . . . . . . . . .

516 517

3. Family LAMIACEAE Lindley 1836 nom. conserv., the Mint Family Ajuga decumbens Thunb. . . . . . . . . . . . . . . . . . Coleus scutellarioides (L.) Benth. . . . . . . . . . . . . Glechoma hederacea L. . . . . . . . . . . . . . . . . . Hyptis suaveolens Poit. . . . . . . . . . . . . . . . . . . Leucas zeylanica R. Br. . . . . . . . . . . . . . . . . . . Ocimum basilicum L. . . . . . . . . . . . . . . . . . . . Orthosiphon stamineus Bth. . . . . . . . . . . . . . . . Prunella vulgaris L. . . . . . . . . . . . . . . . . . . . .

519 520 522 525 526 529 530 531 533

D. Order SCROFULARIALES Lindley 1833

. . . . . . . .

. . . . . . . .

. . . . . . . .

535

1. Family BUDDLEJACEAE Wilhelm 1910 nom. conserv., the Butterfly – bush Family. 535 Buddleja asiatica Lour. . . . . . . . . . . . . . . . . . . . . . 536

xxvi

Contents

2. Family GESNERIACEAE Dumortier 1822 nom. conserv., the Gesneriad Family Aeschynanthus radicans Jack . . . . . . . . . . . . . . . . . Cyrtandra cupulata Ridl. . . . . . . . . . . . . . . . . . . . . Cyrtandra pendula Ridl. . . . . . . . . . . . . . . . . . . . . . Didymocarpus crinitus Jack . . . . . . . . . . . . . . . . . . Didymocarpus platypus C. B. Clarke . . . . . . . . . . . . .

537 538 539 540 541 542

3. Family ACANTHACEAE A. L. de Jussieu 1789 nom. conserv., the Acanthus Family Acanthus ebracteatus Valh . . . . . . . . . . . . . . . . Acanthus ilicifolius L. . . . . . . . . . . . . . . . . . . . Andrographis paniculata Nees . . . . . . . . . . . . . . Asystasia gangetica (L.) T. Anders. . . . . . . . . . . . Barleria prionitis L. . . . . . . . . . . . . . . . . . . . . . Graptophyllum pictum (L.) Griffith . . . . . . . . . . . . Hemigraphis alternata (Burm. f.) T. Anders. . . . . . . Hygrophila angustifolia R. Br. . . . . . . . . . . . . . . . Justicia gendarussa Burm. f. . . . . . . . . . . . . . . . Justicia procumbens L. . . . . . . . . . . . . . . . . . . Lepidagathis incurva D. Don . . . . . . . . . . . . . . . Peristrophe roxburghiana (Schult.) Bremek . . . . . . Pseuderanthemum graciliflorum Nees . . . . . . . . . Rhinacanthus nasutus (L.) Kurz. . . . . . . . . . . . . Ruellia repens L. . . . . . . . . . . . . . . . . . . . . . . Staurogyne setigera (Nees) O. Ktze. . . . . . . . . . .

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542 543 544 546 550 551 552 553 554 555 556 558 559 560 561 562 563

4. Family BIGNONIACEAE A. L. de Jussieu 1789 nom. conserv., the Trumpet-creeper Family Dolichandrone spathacea (L. f.) K. Schum. . . . . . . Oroxylum indicum (L.) Vent. . . . . . . . . . . . . . . . Spathodea campanulata P. Beauv. . . . . . . . . . . . Stereospermum fimbriatum (Wall.) DC. . . . . . . . .

. . . .

. . . .

. . . .

564 566 567 568 569

E. Order CAMPANULALES Lindley 1833 1. Family CAMPANULACEAE A. L. de Jussieu 1789 nom. conserv., the Bellflower Family Codonopsis lancifolia (Roxb.) Moeliono . . . . . . . . . . Laurentia longiflora (L.) Peterm. . . . . . . . . . . . . . . . Lobelia angulata Forst. . . . . . . . . . . . . . . . . . . . . Lobelia chinensis Lour. . . . . . . . . . . . . . . . . . . . . Wahlenbergia marginata (Thunb.) DC. . . . . . . . . . . .

570

. . . . .

571 571 573 573 575 577

Contents

xxvii

2. Family GOODENIACEAE R. Brown 1810 nom. conserv., the Goodenia Family 578 Scaevola taccada (Gaertn.) Roxb. . . . . . . . . . . . . . . 578 F. Order RUBIALES Bentham & Hooker 1873

580

1. Family RUBIACEAE A. L. de Jussieu 1789 nom conserv., the Madder Family Borreria articularis (L. F.) F. N. Williams . . . . . . . . . . . . Canthium horridum Bl. . . . . . . . . . . . . . . . . . . . . . Coptosapelta tomentosa (Bl.) Val. ex K. Heyne . . . . . . . Gynochthodes sublanceolata Miq. . . . . . . . . . . . . . . Hedyotis capitellata Wall. ex G. Don. . . . . . . . . . . . . . Hydnophytum formicarum Jack . . . . . . . . . . . . . . . . Lasianthus stipularis Bl. . . . . . . . . . . . . . . . . . . . . . Morinda citrifolia L. . . . . . . . . . . . . . . . . . . . . . . . . Morinda umbellata L. . . . . . . . . . . . . . . . . . . . . . . Mussaenda mutabilis Hook. f. . . . . . . . . . . . . . . . . . Mitragyna speciosa (Korth.) Havil. . . . . . . . . . . . . . . Nauclea officinalis (Pierre ex Pitard) Merr. & Chun . . . . . Ophiorrhiza communis Ridl. . . . . . . . . . . . . . . . . . . Paederia foetida L. . . . . . . . . . . . . . . . . . . . . . . . . Prismatomeris tetrandra (Roxb.) K. Schk. . . . . . . . . . . Psychotria curviflora Wall. . . . . . . . . . . . . . . . . . . . Randia esculenta (Lour.) Merr. . . . . . . . . . . . . . . . . . Rennellia speciosa (Roxb.) Hook. f. . . . . . . . . . . . . . . Scyphiphora hydrophyllacea Gaertn. f. . . . . . . . . . . . . Urophyllum glabrum Wall. . . . . . . . . . . . . . . . . . . . . G. Order DIPSACALES Lindley 1833

602

1. Family CAPRIFOLIACEAE. L. de Jussieu 1789 nom. conserv., the Honeysuckle Family Lonicera japonica Thunb. . . . . . . . . . . . . . . . . . . . . Viburnum dilatatum Thunb. . . . . . . . . . . . . . . . . . . . H. Order ASTERALES Lindley 1833 1. Family ASTERACEAE Dumortier 1822 nom. conserv., the Aster Family Adenostemma lavenia (L.) O. Ktze. . . . . . . . . . . . . Ageratum conyzoides L. . . . . . . . . . . . . . . . . . . Artemisia vulgaris L. . . . . . . . . . . . . . . . . . . . . . Bidens pilosa L. . . . . . . . . . . . . . . . . . . . . . . . . Blumea balsamifera (L.) DC. . . . . . . . . . . . . . . . .

580 582 583 584 584 585 587 587 588 590 591 591 593 595 596 597 598 599 600 601 601

602 603 605 607

. . . . .

. . . . .

607 609 610 611 613 615

xxviii

Contents

Carpesium abrotanoides L. . . . . . Dichrocephala latifolia (Lamk.) DC. Eclipta prostrata (L.) L. . . . . . . . Elephantopus scaber L. . . . . . . . Emilia sonchifolia (L.) DC. . . . . . Eupatorium fortunei Turcz. . . . . . Eupatorium odoratum L. . . . . . . Galinsoga parviflora Cav. . . . . . . Gnaphalium luteo-album L. . . . . . Gynura procumbens (Lour.) Merr. . Pluchea indica (L.) Less. . . . . . . Saussurea lappa C. B. Clarke . . . Spilanthes acmella (L.) Murr. . . . . Synedrella nodiflora (L.) Gaertn. . Vernonia cinerea (L.) Less. . . . . . Xanthium strumarium L. . . . . . . . Wedelia biflora DC. . . . . . . . . .

. . . . . . . . . . . . . . . . .

. . . . . . . . . . . . . . . . .

. . . . . . . . . . . . . . . . .

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. . . . . . . . . . . . . . . . .

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. . . . . . . . . . . . . . . . .

. . . . . . . . . . . . . . . . .

. . . . . . . . . . . . . . . . .

Class LILIOPSIDA Cronquist, Takhtajan & Zimmermann 1966, the Monocotyledons I. Subclass ARECIDAE Takhtajan 1966 A. Order ARALES Lindley 1833 1. Family ARACEAE A. L. de Jussieu 1789 nom. conserv. the Arum Family Acorus calamus L. . . . . . . . . . . . . . . . . . . . . . . . . Aglaonema oblongifolium (Roxb.) Kunth. . . . . . . . . . . . Alocasia macrorrhiza (L.) G. Don . . . . . . . . . . . . . . . Arisaema japonicum Bl. . . . . . . . . . . . . . . . . . . . . . Pistia stratiotes L. . . . . . . . . . . . . . . . . . . . . . . . . Raphidophora minor Hook. f. . . . . . . . . . . . . . . . . . .

616 618 619 621 623 624 625 626 627 628 629 631 633 635 636 638 639

641 641 641 641 642 644 645 647 648 649

II. Subclass COMMELINIDAE Takhtajan 1966

650

A. Order COMMELINALES Lindley 1833

651

1. Family COMMELINACEAE R. Brown 1810, nom. conserv., the Spiderwort Family Aneilema medicum (Lour.) Kostel. . . . . . . . . . . . . . . Commelina nudiflora L. . . . . . . . . . . . . . . . . . . . . . Floscopa scandens Lour. . . . . . . . . . . . . . . . . . . . . Forrestia griffithii C.B. Clarke . . . . . . . . . . . . . . . . . .

651 652 652 654 654

Contents

xxix

B. Order ERIOCAULALES Nakai 1930

655

1. Family ERIOCAULACEAE Desvaux 1828 nom. conserv., the Pipewort Family 655 Eriocaulon australe R. Br. . . . . . . . . . . . . . . . . . . . . 656 C. Order RESTIONALES J. H. Schaffner 1929

657

1. Family FLAGELLARIACEAE Dumortier 1829 nom. conserv., the Flagellaria Family 657 Flagellaria indica L. . . . . . . . . . . . . . . . . . . . . . . . 657 D. Order CYPERALES G. T. Burnet 1835

658

1. Family CYPERACEAE A. L. de Jussieu 1789 nom conserv., the Sedge family Bulbostylis barbata (Rottb.) Kunth. . . . . . . . . . . . . . . Cyperus brevifolius (Rottb.) Hassk. . . . . . . . . . . . . . . Cyperus cyperinus (Retz.) Suring . . . . . . . . . . . . . . . Cyperus rotundus L. . . . . . . . . . . . . . . . . . . . . . . . Eleocharis dulcis (Burm. f.) Trin. ex Henschel . . . . . . . . Fimbristylis miliacea . . . . . . . . . . . . . . . . . . . . . . .

658 659 660 660 661 662 663

2. Family POACEAE Barnhart 1895 nom. conserv., the Grass family Apluda mutica L. . . . . . . . . . . . . . . . . . . . . . . Arthraxon hispidus (Thunb.) Mak. . . . . . . . . . . . . Bambusa multiplex (Lour.) Raeusch. . . . . . . . . . . Chrysopogon aciculatus (Retz.) Trin. . . . . . . . . . . Coix lacryma-jobi L. . . . . . . . . . . . . . . . . . . . . Cymbopogon citratus (DC.) Stapf . . . . . . . . . . . . Cynodon dactylon (L.) Pers. . . . . . . . . . . . . . . . Eleusine indica (L.) Gaertn. f . . . . . . . . . . . . . . . Imperata cylindrica (L.) P. Beauv. . . . . . . . . . . . . Lophaterum gracile Brongn. . . . . . . . . . . . . . . .

664 665 665 666 667 668 669 672 673 674 675

. . . . . . . . . .

. . . . . . . . . .

. . . . . . . . . .

III. Subclass ZINGIBERIDAE Cronquist 1978

676

A. Order BROMELIALES Lindley 1833

676

1. Family BROMELIACEAE A. L. de Jussieu 1789 nom. conserv., the Bromeliad Family Ananas comosus (L.) Merr. . . . . . . . . . . . . . . . . . . .

676 677

IV. Subclass LILIIDAE Takhtajan 1966

678

A. Order LILIALES Lindley 1833

678

xxx

Contents

1. Family AMARYLLIDACEAE J. St. HILAIRE Agave americana L. . . . . . . . . . . . . . . Crinum asiaticum L. . . . . . . . . . . . . . . Curculigo latifolia Dryand. . . . . . . . . . . . Narcissus tazetta L. . . . . . . . . . . . . . .

. . . .

678 678 680 682 684

2. Family IRIDACEAE A. L. de Jussieu nom. conserv., the Iris Family Belamcanda chinensis (L.) DC. . . . . . . . . . . . . . . . .

685 686

3. Family TACCACEAE Dumortier 1829 nom. Conserv., the Tacca Family Tacca integrifolia Ker-Gawl . . . . . . . . . . . . . . . . . . .

687 688

. . . .

. . . .

. . . .

. . . .

. . . .

. . . .

. . . .

. . . .

4. Family DIOSCOREACEAE R. Brown 1810 nom. conserv., the Yam family 689 Dioscorea hispida Dennst. . . . . . . . . . . . . . . . . . . . 690 B. Order ORCHIDALES Bromhead 1838 1. Family BURMANNIACEAE Blume 1827 nom. conserv., the Burmannia Family Burmannia disticha L. . . . . . . . . . . . . . . . . . . . . . .

692 692 693

Index

695

List of Native Names

705

Appendix

719

Foreword by Norman R. Farnsworth, Ph.D., dr. h.c.(mult.) UIC Distinguished Professor Research Professor of Pharmacognosy College of Pharmacy University of Illinois at Chicago USA

Christophe Wiart has produced a magnificent book covering all pertinent aspects of the potential medicinal plants of the Asia-Pacific Region. Plants (dicots and monocots) are organized by class, subclass, order, family, genus and species. More than 315 species of plants are included in this tome. Botanical descriptions are first given for each family with a general statement of the potential pharmaceutical interest for the family, followed by discussions of the physical characteristics of each species, uses in the region and pharmaceutical interests in the species; the pharmacology, including potential toxicity, of extracts of each plant and an indication of the major pharmacologically active principles with their structures are mentioned. Photographs and/or line drawings are included for each species. I have never seen such a book that has been this carefully prepared, so botanists, chemists, pharmacognosists and pharmacologists having any interest in the medicinal or potentially medicinal higher plants of the Asia-Pacific Region, will be satisfied in the book content. The book will be found useful by academic, industrial and government scientists having any interest in the potential of plants as a source of new drugs.

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Foreword by Professor Nina L. Etkin Past President, International Society for Ethnopharmacology Graduate Chair, Department of Anthropology Department of Ecology and Health — Medical School Associate Editor, Pharmaceutical Biology University of Hawaii, 2424 Maile Way Honolulu, Hawaii 96822 USA

“Medicinal plants of Asia-Pacific: Drugs for Future?” offers researchers a strong foundation from which to advance the field of ethnopharmacology. The challenge is to use the information contained herein in meaningful ways to understand the conjunction of medical ethnography and the biology of therapeutic action. An impediment to predicting the structure and content of an ethnopharmacology of the future is to identify objectives for a field whose self-identified membership represents various academic and applied disciplines, as well as commercial interests. At present, most ethnopharmacology research is conducted by investigators trained in anthropology, botany, pharmacognosy, and pharmacology. Other contributors include biochemists, researchers in veterinary medicine, clinicians, and historians of science. In the past, this multi-but not trans-disciplinarity has embodied substantial disparities, which challenged efforts to harmonize objectives and coordinate methodologies. At the same time these disparities underlie a dynamic tension that inspires discussion and collaborations for the future. My own perspective on ethnopharmacology resonates the voices that forged the International Society for Ethnopharmacology (ISE), and later the mission statement of the ISE’s official journal: the Journal of Ethnopharmacology (JEP) encourages scholarly and applied research “concerned with the observation, description and experimental investigation of indigenous drugs and their biological activity.” Despite this call for convergence across a range of natural and social sciences, most of what was published as ethnopharmacology in the last few decades more closely approximates pharmacognosy xxxiii

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Foreword

and pharmacology, than it does transdisciplinary research. Privileging bioscientific ideologies and technology reproduces a Euro-American tradition that discounts traditional ways of knowing i.e., the implicit assertion that medicines become meaningful only when validated by pharmacologic inquiry. In an integrated ethnopharmacology of the future, bioscience would instead serve as one of the several lenses through which we understand how people manage resources and health. These comprehensive data on the medicinal plants of Asia and the Pacific represent the kind of reference material that encourages researchers in ethnopharmacology to project these findings against some higher level of abstraction, in order to better comprehend human-plant relations.That is to say, advancing scholarship and application of ethnopharmacology will require more than incremental growth through collection of technical data. For instance, this book can be used by researchers to explore how traditional knowledge and management of Pacific and Asia resources are culturally constructed and socially negotiated in ways that impact human health; how the use of plants in overlapping contexts such as food and medicine influences both local ecologies and human health; or how the diverse microecologies of diverse Pacific populations influence medicinal cultures. An integrated, theory- and issue-driven ethnopharmacology will advance beyond multidisciplinary (parallel streams), to interdisciplinary (some theoretical and methodological exchange across disciplines), to transdisciplinary research that integrates the perspectives and tools of diverse disciplines. Further, we can hope that in the future, ethnopharmacology research will be contextualized to broader issues of biodiversity conservation, sustainable resource management, and intellectual and biological property rights.

Foreword by Professor Elizabeth M. Williamson The School of Pharmacy University of Reading Whiteknights, Reading Berkshire, RG6 6AJ

This new volume, Medicinal Plants of Asia-Pacific: Drugs for Future?, by Christophe Wiart, represents a huge and important undertaking, since much of the flora of this area of the world, while well-known locally as a source of medicines, has been neglected in terms of scientific evaluation. Public interest in traditional forms of herbal medicine, and in Asian medicine in particular, continues to grow and not only do many people — over 80% of the world population in fact, rely upon herbal medicines for their healthcare needs, but further investigations into the potential of the species covered in this book may lead to the discovery of novel drugs of global importance. The medicinal flora of the Asia-Pacific region embodies a virtually untapped reserve of original molecules which await isolation, and chemical and pharmacological investigation. Such development may also deliver a valuable asset for local people, who can then benefit from the exploitation of their natural resources. Furthermore, some of these plants are endangered species, and documentation of their potential usefulness may help to ensure their conservation, and perhaps even lead to programmes for sustainable development. The book includes 429 species found from India to Hawaii, all covered in commendable depth, and most beautifully illustrated. For all entries, botanical and taxonomic details are given, including synonyms and even some phylogenetic information about the order and plant family. The description of the plant is comprehensive enough to allow for identification, and is aided by photos and drawings. The pharmaceutical uses are dealt with in a thorough manner, the chemistry explained and supplemented with more than 300 chemical structures, and about 2500 bibliographic references. Trained as a pharmacist in France and having worked in the French pharmaceutical industry, (isolating, purifying and determining the structures of new xxxv

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Foreword

bioactive compounds from plants.) Christophe Wiart is an experienced phytochemist. For many years now, he has been a scientist at the University of Malaysia, involved with the Malaysia tropical rainforest plant screening programme and managing expeditions in primary and secondary tropical rainforest. His work includes the collection of plants, identification of them and preparation for the herbarium, as well as phytochemical and pharmacological evaluation for drug discovery. He has published many scientific papers devoted to the discovery of new natural compounds, and has written several books on the subject of medicinal plants. This wide experience has given him a broad perspective on drug discovery from plants, and has benefited this book enormously. It will be an invaluable resource for doctors, pharmacists, plant scientists, pharmaceutical companies and conservationists in the region, and to all who are interested in medicinal plants.

DIVISION MAGNOLIOPHYTA CRONQUIST, TAKHTAJAN & ZIMMERMANN 1966, THE ANGIOSPERMS OR FLOWERING PLANTS

The division Magnoliophyta consists of 2 distinct classes, the Magnoliopsida and the Liliopsida, which are believed to have appeared some 130 million years ago. The Magnolopsida is the largest and oldest class.

Part I: Class MAGNOLIOPSIDA Cronquist, Takhtajan & Zimmermann 1966, the Dicotyledons The class Magnoliopsida consists of 6 subclasses, 64 orders, 318 families, and about 165,000 species of plants which have evolved from aquatic weeds forced to adapt to dry climatic conditions. The Magnoliidae is the most primitive subclass of Magnoliopsida (Appendix I) and a common archaic ancestor for all existing dicotyledons.

I. Subclass MAGNOLIIDAE Takhtajan 1966 The Magnoliidae consists of 8 orders, 39 families and about 12 000 species of primitive trees, shrubs or woody climbers confined in primary rainforests. The flowers of Magnolidae are often large, and made up of an indefinite number of free carpels, stamens, petals and sepals. The orders Magnoliales, Laurales and Ranunculales make up more than two-thirds of the species of Magnoliidae. The chemical weapons used here are isoquinoline alkaloids which bind to protein receptors of neurones and impede or promote neurotransmission. Besides, isoquinolines are amphiphile and penetrate bacteria wherein are inactivated enzymes and 1

2

Division MAGNOLIOPHYTA

DNA. The ability of alkaloids to bind to cellular receptors often explains the medicinal and toxic properties of plants and their pharmaceutical interest.

A. Order MAGNOLIALES Bromhead 1838 The order Magnoliales is the most primitive order of the subclass Magnoliidae (Appendix I).This order consists of 10 families and about 3000 species of trees or shrubs, the therapeutic potential of which is still waiting to be discovered. Magnoliales are living fossils rich in isoquinolines and indoles alkaloids, lignans, essential oils, diterpenes, triterpenes, tannins, and phenylpropanoids. Of particular interest in this order are alkaloids which might hold potentials for the treatment of cancers, microbial infections, anxiety, mood disorder, hypertension and Alzheimer’s and Parkinson diseases.

1. Family HIMANTANDRACEAE Diels 1917 nom. conserv., the Himantandra Family The family Himantandraceae consists of the single plant Galbulimima belgraveana (F. Muell.) Sprague. Galbulimima belgraveana (F. Muell.) Sprague Physical description: It is a tree which Synonymy: Himantandra grows to a height of 35 m and which belgraveana (F. Muell.) F. Muell. has a girth of 60 cm. The plant is comCommon name: Pigeon berry ash, mon in the mountain rainforests of Papua agara, white Magnolia. New Guinea, Australia and Indonesia. The buttresses can reach up to 3 m, with a width of 1 m and a thickness of 5 cm–20 cm. The bark is greenish brown, bitter, and has a resinous smell. The inner bark is cream-colored and rapidly turns red-brown when exposed to light. The wood is white or pale yellow and very soft. The sap-wood and heart-wood are white to a pale straw color. The stems, underside of leaves, petioles, inflorescences and fruits are densely to sparsely covered with copper-colored peltate scales. Leaves: the leaves are simple, alternate and estipulate. The petiole is 1.3 cm–1.5 cm long, channeled and glabrous. The blade is elliptic, oblong, hard, 14 cm × 5.7 cm, glossy green above and silvery brown below. The midrib is sunken above and prominent below. The margin of the blade is recurved. The blade shows 13–15 pairs of indistinct secondary nerves. The flowers are bisexual, large, and have a strong unpleasant odour. The perianth is white, cream or brown. The fruits are pink or red drupes which are 1.5 cm–3 cm in diameter. The fruit pedicel is 2.5 cm long (Fig. 1).

Subclass Magnoliidae

3

Fig. 1. Galbulimima belgraveana (F. Muell.) Sprague. From: KLU Herbarium 33852, Flora of Sulawesi (Celebes). Ex Herb. Leiden Indonesian. Dutch Expedition 1979. Field collector & botanical identification: V Balgooy, 11.7. Geographical localization: South Sulawesi 2◦ 15 –3◦ 3 South — 121◦ –121◦ 45 East, behind Inco driving, altitude: 500 m. Center near Nickel Plant, disturbed forest on ultrabasic soil.

O

O

O

O

+ N

N

(+) - Himbacine

Acetylcholine

Pharmaceutical interest: The medicinal Uses: In Papua New Guinea, properties of Galbulimima belgraveana (F. a decoction of bark of GalbuMuell.) Sprague are attributed to piperidine limima belgraveana (F. Muell.) alkaloids, such as (+)-himbacine, which are Sprague is drunk to invigorate structurally shaped like acetylcholine and health before war, and to give are therefore muscarinic receptor antagohallucination and premonition. nist/agonist (Zholos AV et al., 1997). These anticholinergic alkaloids have become the focus of attention as a potential source of drugs for the treatment of Alzheimer’s diseases, cardiac bradycardia and glaucoma. Reference Zholos AV, et al. (1997) Br J Pharmacol 122(5): 855–893.

Caution: This plant is toxic.

4

Division MAGNOLIOPHYTA

2. Family ANNONACEAE A. L. de Jussieu 1789 nom. conserv., the Custard-apple Family Physical description: The family Annonaceae consists of about 120 genera and over 2000 species of tropical trees, shrubs or climbers making up about three-fourths of the order Magnoliales. The bark of Annonaceae is fibrous and fragrant. The leaves are simple, alternate, and without stipules. The flowers consist of a thalamus to which are inserted 3 sepals, 2 whorls of 3 petals, an indefinite number of short and compressed stamens and numerous free carpels. The fruits are ripe carpels. Pharmaceutical interest: Examples of Annonaceae are Annona reticulata L. (custard apple), Annona cherimola (cherimoya), and Annona squamosa L. (sweetsop), the fruit of which are palatable. Another example is Cananga odorata (lmk.) Hook. f. & Thoms. the essential oil of which (ylang-ylang) is used to make perfumes. Annonaceae have attracted a great deal of interest on account of their ability to elaborate secondary metabolites which might hold potential for the treatment of cancer, bacterial infection, hypertension and brain dysfunctions. O Acetogenins: A number of plants O OH OH OH O classified within the genera AnnO OH ona, Asimia, Goniothalamus, PolyAcetogenin althia, Rollinia, Uvaria and Xylopia contain a unique type of lipidrelated substances consisting of 35–39 carbons, 1 or 2 tetrahydrofurane rings, a terminal γ -lactone and oxygen functions. These compounds are difficult to extract but are worth being studied as they kill eukaryotic cells by impeding the enzymatic activity of NADH-ubiquinone reductase (complex-I) [NADH dehydrogenase (ubiquinone)] which is normally responsible for the mitochondrial electron transport or cellular respiration. A classical example of acetogenin is bullatacin from Annona bullata. Bullatacin displays cytotoxic potencies a number of order of magnitude greater than those of adriamycine (doxorubicin) and has been patented as a clinicalanti-tumor agent.

Isoquinoline alkaloids: isoquinoline (aporphines) alkaloids bind to the cellular receptors of serotonine, dopamine, acetylcholine and noradrenaline. This property is attributed to the fact that the chemical structure of isoquinolines is similar to that of neurotransmitters (Fig. 2). Aporphine alkaloids, being an α1 -adrenoreceptor antagonist or partial agonist, and a calcium channel blocker

Subclass Magnoliidae

5

NH2

NH HO

N H Isoquinoline alkaloid

HO

HO

Serotonine

NH2

OH

NH2

HO

Noradrenaline

OH Dopamine

Fig. 2. Examples of neuroactive natural products characterized from the family Annonaceae. Note the similitude of chemical structure of isoquinoline alkaloids with serotonine, dopamine and noradrenaline.

or 5-hydroxytryptamine (5HT2 ) antagonist, might hold potential for the treatment of hypertension. A number of isoquinoline alkaloids, being a muscarinic blocker, 5-hydroxytryptamine (5HT1 ) receptor agonist or dopamine reuptake inhibitor, might hold potential for the treatment of asthma, gastric ulcer, anxiety or depression. Terpenes and flavonoids: Clerodane and kaurane diterpenes characterized from Polyalthia and Annona, as a well as chalcones and flavanones characterized from Desmos, Fissistigma, and Uvaria species are cytotoxic and antimicrobial. In the Asia-Pacific, about 50 species of Annonaceae are used for medicinal purposes, particularly to treat fever, to assuage stomachaches, to facilitate abortion and to treat skin diseases. Anaxagorea javanica Bl. [Anaxagoras = Greek philosopher; Latin javanica = from Java] Physical description: It is a treelet Synonymy: Anaxagorea scortechinii of the lowland rainforest of Malaysia, King. Borneo and Java. The bark is slightly Common name: Champoon (Thai). fissured and yellowish. Leaves: simple, alternate and exstipulate. The petiole is 5 mm–1 cm long, transversally fissured and channeled above. The blade is leathery, 7 cm–18 cm × 4 cm–6 cm, and oblong-lanceolate. The apex of the blade is acute or slightly acuminate and the base is tapering. The margin is slightly recurved and wavy. The blade shows 6–10 pairs of secondary nerves.

6

Division MAGNOLIOPHYTA

The flowers are fragrant, grouped by 1–4, terminal and opposite the leaves. The calyx comprises of 2–3 sepals which are valvate. The corolla consists of 6 petals which are valvate and arranged in 2 distinct whorls.The outer petals are elliptic with a broad base, greenish outside and white inside. The inner petals are white with narrow claw and rhomboid blade. The gynecium consists of 8–9 angled distinct carpels. The stigmas are conical with U-shaped opening at the apex. The fruits are bunches of 4–8, light-green, clubshaped, succulent and dehiscent 5 cm long ripe carpels radiating from the thalamus. Each carpel contains a pair of glossy and pure black, tear-shaped, and 5 mm long seeds (Fig. 3).

Fig. 3. Anaxagorea javanica Bl.

Pharmaceutical interest: Bioassay-guided Use: A decoction of the root of fractionation of a methanolic extract of Anaxagorea javanica Bl. is drunk heartwood of Anaxagorea luzonensis reby Malays to aid recovery from sulted in the isolation of a nonsteroidal childbirth. phytoestrogens: 8-isopentenylnaringenin (Kitaoka M et al., 1998). 8-Isopentenylnaringenin injected into ovariectomized rats (30 mg/Kg/day) completely suppresses bone and uterine changes as effectively as 17-β-estradiol (Masaaki M et al., 1998). The pharmacological potential of Anaxagorea javanica Bl. is unknown. O

OH HO

O OH

HO 8 Isopentenylnaringenin

Estradiol

References Kitaoka M, et al. (1998) Planta Med 64(6): 511–515. Masaaki M, et al. (1998) Planta Med 64(6): 6516–6519.

Warning: This plant may have some estrogenic properties and potentially increase the risk of breast cancer.

Subclass Magnoliidae

7

Annona muricata L. [From Latin, annona = yearly produce and muricata = muricate] Physical description: It is a fruit Common names: Sour sop; tree native to tropical America, probcorrossolier (French), pulippala ably introduced in the very early (Tamil); mempisang, durian b’landa, times by the Spaniards. The leaves: sri kaya blanda, nona blanda (Malay); simple, alternate, exstipulate and goyabrano, guanabano (Filipino); mak 5.5 cm–18 cm × 2 cm–7 cm. The blade khieb thet, mang can xiem, tiep is oblong, lanceolate-obovate, often parang (Vietnamese). shortly acuminate at the apex, and sparingly appressed and hairy beneath. The flowers are at first green, then ripening into yellowish-pale. The outer petals are 3.5 cm–5 cm long, acuminate, when the inner ones are imbricate, obtuse and 2.5 cm–3.5 cm long. The stamens are 4 mm–5 mm long and the carpels are numerous and free. The fruits are heart-shaped, muricate, green, 15 cm–35 cm × 10 cm–15 cm and edible (Fig. 4). Pharmaceutical interest: Cytotoxic property: In regards to the cytotoxic property of Annona muricata L., a number of experiments conducted in vitro have clearly

Fig. 4. Annona muricata L.

Uses: The tanniferous unripe fruits and bark of Annona muricata L. are eaten so as to stop dysentery and diarrhea. In Indonesia, the crushed leaves are applied externally to heal boils and a powder of the dried leaves is used to kill insects. A decoction of the leaves is drunk to expel intestinal worms. In Malaysia, a liquid preparation containing the leaves is applied externally to treat rheumatism, and to alleviate cough and fever. A poultice of the powdered leaves is applied externally to soothe inflamed parts and to treat skin diseases. In the Philippines, the green bark is applied externally to heal wounds and to stop bleeding, and a decoction of the leaves is used to wash ulcers and to heal wounds. In Vietnam, an infusion of leaves is drunk to combat anxiety. In India, the oil expressed from the seeds is applied to the hair to kill lice, but it burns the eyes.

8

Division MAGNOLIOPHYTA

demonstrated that acetogenins are drastically antineoplastic. Annopentocins A–C, cis- and trans- annomuricin D-one inhibit the proliferation of lung carcinoma cells (A549), colon cells (HT29) and pancreatic cells (PACA) cultured in vitro, with potencies equal to or greater than that of adriamycin (Bories C et al., 1991; Liaw CC et al., 2002). Neurological properties: Anonaine, nornuciferine, and asimilobine from Annona muricata L., block 5-hydroxytryptaminergic (5HT1 A) receptors (Hasrat JA et al., 1997) thereby substantiating the anxiolytic use of the plant. Such a property is not surprising since the molecular structures of anonaine, nornuciferine and asimilobine are similar to that of serotonine. 5-Hydroxytryptaminergic (5HT1 A) receptors mediate in the central nervous system the autonomic control of hypothermia, hyperphagia, analgesia, blood pressure, venereal desire, anxiety and several behavioral paradigms. It has been hypothesized that the anxiolytic property of buspirone is on account of a blockade of 5-hydroxytryptaminergic (5HT1 A) receptors. Methysergide, a partial 5-hydroxytryptaminergic (5HT1 ) agonist, and sumatriptan, a 5-hydroxytryptaminergic (5HT1 D) agonist, are drugs used to assuage headache. There is an expanding body of evidence to suggest that over representation of atypical Parkinsonism and progressive supranuclear palsy in the French West Indies could be due to the ingestion of Annona muricata L. A case-control work carried on 87 patients with Parkinsonism indiFig. 5. Hypothetic mechanism of action of cates that 29 patients with progressive Annona muricata L. alkaloid on the central ner- supranuclear palsy and 30 patients vous system via blockage of dopaminergic D2 with atypical Parkinsonism were regreceptors in the basal ganglia. ACH: acetylularly ingesting the fruit of Annona choline; ALK: alkaloid of Annona muricata; C: cortex; DA: dopamine; GP: globus pallidus; SM: muricata L. (Caparros-Lefebvre D striated muscle; P: putamen; SN: substancia et al., 1999). Movement disorder nigra; T: thalamus. is a symptom of extrapyramidal motor

Subclass Magnoliidae

9

dysfunction and a prominent manifestation of diseases affecting the basal ganglia. The basal ganglia receives impulses from different parts of the cerebral cortex and plays a key role in the control of movement. The basal ganglia consists of the caudate nucleus, putamen, globus pallidus, substancia nigra and subthalamic nucleus, which are interconnected by dopaminergic and cholinergic neurons, deep within the cerebral hemispheres (Fig. 5). Under normal condition, the dopaminergic system inhibits the cholinergic output. In the case of Parkinsonism, the dopaminergic neurons of the substancia nigra fail to control the cholinergic output, thus resulting in tremors, rigidity and akynesia. Antipsychotic drugs reducing the concentration of striatal dopamine (reserpine) or blocking the dopaminergic D2 receptors (phenothiazines and butyrophenones) are well-known to cause Parkinsonism. Are anonaine, nornuciferine, and asimilobine able to block the dopaminergic D2 receptors of the basal ganglia or do they enhance the cholinergic activity? Ingestion of Annona muricata L. causes galactorrhea and tremors (Rom’an G, 1998), two typical symptoms of dopamine D2 blockade. Oxoaporphine, aporphine, and a series of phenanthrene alkaloids characterized from Annona purpurea inhibit significantly the aggregation of platelets (Chang FR et al., 1998), suggesting the inhibition of phospholipase A2 . H3CO

HO

H3CO

Asimilobine

NH

NH

H3CO

Nornuciferine

References Bories C, et al. (1991) Planta Med 57(5): 434–436. Caparros-Lefebvre D, et al. (1999) Lancet 354 (9175): 281–286. Chang FR, et al. (1998) J Nat Prod 61(12): 1457–1461. Hasrat JA, et al. (1990) J Pharm Pharmacol 49(11): 1145–1149. Liaw CC, et al. (2002) J Nat Prod 65(4): 470–475. Rom’an G. (1998) Curr Opin Neurol 11(5): 539–544.

Warning: Cases of association of cancer (due to tannins) and Parkinsonism (due to alkaloids) following ingestion of Annona muricata L. are possible. Artabotrys suaveolens Bl. [From Greek, artao = support and botrys = bunch of grapes and suavis = sweet] Physical description: It is a rainforest climber of Burma, Java, Moluccas and the Philippines. The bark is blackish and smooth and the stems are hooked.

10

Division MAGNOLIOPHYTA

Leaves: simple, alternate and exstipulate. The petiole is glabrous, channeled and 3 mm–5 mm long.The blade is dark green, glossy, glabrous, leathery, elliptic and 8.5 cm×3.5 cm–5 cm× 3 cm. The apex of the blade is acuteacuminate; the base is tapering; and the margin is entire and slightly acuminate. The flowers are 1 cm long, whitish and tomentose.The calyx comprises of 3 sepals which are ovate, acute and 2.5 mm long. The corolla comprises of 2 distinct whorls of 3 petals which are valvate. The petals are dilated at the base, and develop a cylindrical limb and a recurved apex. The fruits are green, glossy, ellipsoid, 1.4 cm × 5 mm ripe carpels, each containing a single seed (Fig. 6).

Fig. 6. Artabotrys suaveolens Bl.

Pharmaceutical interest: The pharCommon name: Akar cenana (Malay). macological properties of Artabotrys suaveolens Bl. are unexplored. One Uses: In Malaysia and Indonesia, an might set the hypothesis that isoquinoinfusion of the leaves provides an line alkaloids, such as artabotrine, aromatic drink used to treat cholera. In suaveoline and artabotrinine, could the Philippines, a decoction of the bark be responsible for both antibacteand roots is drunk to promote menses rial and emmenagogue properties and to aid recovery from childbirth. (Maranon J, 1929; Barger G et al., 1939; Santos AC et al., 1932). Artabotrine from Artabotrys zeylanicus alleviates yeast cells cultured in vitro (Wijeratne EMK et al., 1995). Both liriodenine and atherospermidine characterized from Artabotrys uncinatus are cytotoxic in vitro (Wu YC et al., 1989). The leaves of Artabotrys odoratissimus display an antifertility property (Chakrabarti B et al., 1968). Norstephalagine and atherospermidine characterized from the bark of Artabotrys maingayi relax rat uterine KCl- and oxytocin-induced contractions induced by potassium chloride and the rhythmic contractions induced by oxytocin (Cortes D et al., 1990). Antiplasmodial property: An interesting feature of the genus Artabotrys is the production of antimalarial sesquiterpenes peroxides. One such compound is yingzhaosu A, from Artabotrys uncinatus, a plant used in India to make aromatic tea. Arteflene, a synthetic peroxide developed from yingzhaosu A given (single oral dose 25 mg/Kg) in a phase 3, open-labeled randomized clinical

Subclass Magnoliidae

11

trial, was not effective in curing Plasmodium falciparum malaria (Radloff PD et al., 1996). O O

O

OH O HO

F3C

O

CF3

Arteflene

Yingzhaosu

References Barger G, et al. (1939) J Chem Soc (London), 991–997. Chakrabarti B, et al. (1968) J Ind Med Assoc 51(5): 227–229. Maranon J. (1929) Philip J Sci 38: 259–265. Radloff PD, et al. (1996) Am J Trop Med Hyg 55(3): 259–262. Santos AC, et al. (1932) Nat Appl Sci Bull (Univ Philip) 2: 407–415. Wijeratne EMK, et al. (1995) Tetrahedron 51(29): 7877–7882. Wu YC, et al. (1989) Phytochem 28(8): 2191–2196.

Warning: Caution must be taken as the toxic effects of this plant are unknown. Cananga odorata (Lamk.) Hook. f. & Thoms. [From Malay, kananga = Canangaodorata (Lamk.) Hook. f. & Thoms. and from Latin, odorem = odour] Physical description: It is a shrub which grows to a height of 4 m. The plant grows wild in a geographical zone spanning from India to Polynesia.The bark is blackish to grey, smooth and the young stems are pubescent. Leaves: simple, alternate and exstipulate. The blade is light green, soft, dull, oblong to broadly elliptic, and 6.5 cm × 20 cm–3 cm × 8.5 cm. The apex of the blade is acuminate and the base is round. The blade shows 6–10 pairs of secondary nerves. The flowers are strongly fragrant. The calyx consists of 3 sepals and the corolla consists of 6 linear valvate petals, yellow at first then turning golden yellow. The fruits consist of 2 to 12 ripe carpels arranged in 2 whorls, ripening to black, and 1.75 cm × 2.5 cm. Each carpel contains 6 to 12 seeds (Fig. 7). History: The oil obtained by distillation of the flowers is the Cananga oil or ylang-ylang oil, which is used to make perfumes. Cananga oil added to coconut oil and other ingredients makes the Macassar oil which was so familiar to the well-groomed Victorian and Edwardian males. The British Standards Institution has published standard specifications for Cananga oil (BS 2991/ 1:1965). Cananga oil contains geraniol, linalool esters of acetic and benzoic acids, p-cresol methyl ester, cadidene, some sesquiterpenes and phenols (Greenberg LA et al., 1954).

12

Division MAGNOLIOPHYTA

Synonymy: Canangium odoratum Baill. Common names: Ylang-ylang tree; bois de lance batard (French); maladi (Tamil); kenanga (Malay); kadapnyan (Burmese).

Pharmaceutical interest: Cytotoxic properties: Cananga odorata (Lamk.) Hook. f. & Thoms. contains a cytotoxic oxoaporphine alkaloid known sas liriodenine, which Fig. 7. Cananga odorata (Lamk.) Hook. f. & inhibits the enzymatic activity of topoi- Thoms. somerase II in vitro and in vivo (Woo S et al., 1997).The inhibition of topoisomerase II, a key enzyme of the DNA replication, causes a quick cleavage of the DNA backbone and thereby cellular death. Topoisomerase II inhibitors are of critical chemotherapeutic importance and the family Annonaceae, which abound with liriodenine-like alkaloids, may appear as a potential reserve of chemotherapeutic agents. Examples of therapeutic topoisomerase II inhibitors are the relatively newly introduced oral antibacterial broad-spectrum antibiotic fluoroquinolones. An example of fluoroquinolone is ciprofloxacine, generally regarded as the most significant development in the field of antibacterial chemotherapy. The fruits contain some alkaloids, and sesquiterpenes which have cytotoxic properties (Hsieh TJ et al., 2001). Amebicidal properties: An extract of Cananga odorata (Lamk.) Hook. f. & Thoms. inhibits, in vitro, the proliferation of Acanthameba culbertsoni, Acanthameba castellani, and Acanthameba polyphaga which are the causative agents of granulomatous amoebic encephalitis and amoebic keratitis (Chu DM et al., 1998). References

O N

O

O

Liriodenine

Chu DM, et al. (1998) Parasitol Res 84(9): 746–752. Greenberg LA, et al. (1954) Handbooks of Cosmetic Materials, Interscience, New York. Hsieh TJ, et al. (2001) J Nat Prod 64(5):616–619. Schieffelin, et al. (1973) Almay Hypo-allergenic Cosmetics Product Formulary, 8th ed. Pharmaceutical Laboratories Division, New York. Woo S, et al. (1997) Biochem Pharmacol 54(4): 467–473.

Warning: Perfumes containing Cananga oil can produce dermatitis in sensitized individuals and have been removed from certain cosmetics (Greenberg LA et al., 1954; Schieffelin, 1973).

Subclass Magnoliidae

13

Cyathostemma argenteum (Bl.) J. Sinclair [From Latin, argentum = silver] Physical description: It is a rainforest Synonymy: Uvaria micrantha Hook. f. climber of Malaysia and Indonesia.The & Thoms. young stems are rufous-pubescent. Leaves: simple, alternate and exstipulate.The blade is oblong-lanceolate, 10 cm–17 cm×4 cm–6 cm, slightly silverygrey puberulous beneath and glabrous above, except the midrib. The base of the blade is broad, round, truncate and the apex is shortly and obtusely acuminate. The petiole is 3 mm–5 mm long. The flowers are dark purple. The corolla consists of 6 petals which are broadly ovate, obtuse, 5 mm long, imbricate, pubescent and inflexed at the apex. The calyx comprises of 3 sepals which are broadly ovate, obtuse, and 2 mm long. The fruits are sausage-shaped and 2 cm × 4 cm. Pharmaceutical interest:

Uses: In Indonesia, the bark is used to

stop spasms and to soothe inflamed Antispasmodic properties: Isoquinoparts. The flowers are used to treat line alkaloids in Cyathostemma argenmalaria, and the seeds are eaten to teum (Bl.) J. Sinclair and in other assuage stomach discomfort and to Annonaceae probably explain the frecombat fever. In Malaysia, a paste quent use of these plants to stop of the fresh flowers is applied to the spasms. One such alkaloid, from Fischest to treat asthma. In the Solomon sistigma glaucescens, is (-)-discreIslands, a paste of the leaves is used tamine which inhibits, experimentally, externally to heal boils. In India, the essential oil makes an external remthe contraction of rat aorta induced edy used to treat cephalgia, ophtalmia by noradrenaline, phenylephrine, and and gout. clonidine. (-)-Discretamine inhibits the irreversible blockade of α-adrenoreceptors by phenoxybenzamine and inhibits the formation of [3 H]-inositol monophosphate caused by noradrenaline, appearing, therefore, as a selective α1 -adrenoreceptor blocking agent. (-)-Discretamine blocks non-competitively 5-hydroxytryptamine (5HT) receptors (Ko FN et al., 1994).

Cytotoxic properties: (-)-Discretamine inhibits the proliferation of brine shrimps (LC50 > 125 µg/mL) less efficiently than emetine (LC50 : 30 µg/mL; Khamis SB et al., 1998). Cyathostemmine, from Cyathostemma viridifolium, inhibits the proliferation of KB cells cultured in vitro (IC50 = 4.5 µg/mL; Mahmood K et al., 1993).

HO H3CO

N OCH3 OH Discretamine

14

Division MAGNOLIOPHYTA

References Khamis SB, et al. (1998) J Pharm Pharmacol 50: 281. Ko NK, et al. (1993) Br J Pharmacol 110: 882–888. Mahmood K, et al. (1993) Nat Prod Lett 3: 245–249.

Warning: Caution must be taken as the toxic effects of this plant are unknown. Desmos chinensis Lour. [From Greek, desmos = a bundle and from Latin, chinensis = from China] Physical description: It is a handSynonymy: Unona discolor Vahl some treelet which grows wild in a Common names: Chinese Desmos; geographical zone spanning from the kenanga hutan, akar darah, akar Himalayas to China and the Asiamariam (Malay). Pacific. The bark is lenticelled. Leaves: simple, alternate and exstipulate. The Uses: In Malaysia, a decoction of blade is 3 cm–2 cm × 7 cm–15 cm, very the roots of Desmos chinensis is thin, oblong, glaucous below and round drunk to stop diarrhea, dysentery, to at the base and shows 8–10 pairs of treat vertigo and to aid recovery secondary nerves. The petiole is 5 mm– from childbirth. In Vietnam, Desmos 8 mm long. The flowers are solitary, chinensis Lour. is used to treat cold. sweet scented, showy, facing the leaves and attached to 3 cm–5 cm long pedicels. The sepals are 5 mm–1 cm long. The petals are valvate, greenish yellow and 4 cm–8 cm long.The fruits are strings of greenish to reddish, 3 cm–4 cm × 1 cm–1.5 cm beads. The pedicels are 1 cm– 1.5 cm long (Fig. 8). Pharmaceutical interest: Desmos chinensis has attracted a great deal of interest on account of its ability to elaborate C-benzylated chalcones (Rahman MM et al., 2003). Antibacterial and leishmaniacidal properties: 5-methoxy-7-hydroxyflavanone and 6 -hydroxydehydrouvaretin characterized from Desmos chinensis Lour. inhibit the proliferation of Bacillus subtilis and Shigella boydii cultured in vitro. 5-methoxy7-hydroxyflavanone inhibits the proliferation of Staphylococcus aureus and

Fig. 8. Desmos chinensis Lour.

Subclass Magnoliidae

15

6 -hydroxydehydrouvaretin is active against the flagellated protozoan Leishmania donovanii (Nazmul Q et al., 1996). 2 , 4 -dihydroxy-6 -chalcone and chrysin characterized from Desmos chinensis Lour. inhibit the proliferation of several sorts of Gram-positive bacilli and Gram-negative bacilli (Qais N et al., 1997). Tyrosine kinase property: 8 formyl-2,5,7trihydroxy-6-methylflavanone characterized O from Desmos chinensis Lour., inhibits tyro- HO sine kinase in the epidermal growth factor receptor-over expressing NIH3T3 (ER12) cells, and inhibits the formation of inositol OCH3 O phosphate induced by the epidermal growth factor (Kakeya H et al., 1993). Inhibitors of 5 - Methoxy - 7- hydroxyflavanone tyrosine kinase could help to suppress the development of tumors and breast carcinoma. References Kakeya H, et al. (1993) FEBS Lett 320(2): 169–172. Nazmul Q, et al. (1996) Banglad J Bot 25(2): 155–158. Qais N, et al. (1997) Fitoter 67(6): 554–555. Rahman MM, et al. (2003) Fitoter 74(5): 511–514.

Warning: Caution must be taken as the toxic effects of this plant are unknown. Fissistigma species [From Latin, fiss = cleave and from Greek, stigma = mark made by pointed instrument] Physical description: Fissistigma species are woody climbers with the dorsal side of sepals and petals, ovaries, ripe carpels, apices of stems and petiole densely covered with a golden-brown tomentum. The flowers are often large and comprise of 3 valvate sepals and 6 valvate petals in 2 whorls, the inner ones being smaller. The fruits are large, globose and thick-walled free Uses: Malaysians have been known carpels, each carpel containing 1–8, to drink decoctions of Fissistigma glossy and brown seeds (Fig. 9). manubriatum (Hook. f. & Thoms.) Merr. Pharmaceutical interest: Muscarinic properties of liriodenine: One might set the hypothesis that Fissitigma species assuage stomachaches on account of isoquinoline

(Melodorum manubriatum Hook. f. & Thoms.), Fissistigma lanuginosum or Fissistigma kingii to assuage stomachaches, and the leaves of Fissistigma fulgens are applied externally to soothe inflammation.

16

Division MAGNOLIOPHYTA

alkaloids, such as liriodenine, which are known to block muscarinic receptors and therefore impede both the secretion of gastric juices and the contraction of the gastric smooth muscles. Liriodenine (an oxoaporphine), characterized from Fissistigma glaucescens, inhibits the contraction of isolated portions of guinea-pig trachea induced by carbachol. Liriodenine is slightly more potent than methocramine but less potent than atropine, pirenzepine and 4-diphenylacetoxy-N-methylpiperidine. Liriodenine (300 µM) partially inhibits the contraction induced by potassium, leukotriene C4 , neurokinin A, prostaglandine F2 α, histamine and U46619. Liriodenine does not affect the tracheal contraction induced U46619 and neurokinin in the presence of nifedipFig. 9. Fissistigma latifolium (Dunal) Merr. var. ine (1 µM) or in the presence of a ovoideum. calcium-free medium, and it has no effect on the cAMP and cGMP content of the trachea. Liriodenine is a selective muscarinic receptor antagonist in isolated portions of ileum and cardiac preparations (Lin C et al., 1994). Liriodenine has inotropic positive property and is a potential candidate for the treatment of cardiac arrhythmia (Lin C et al., 1993). Further experiments using whole-cell voltage clamp show that liriodenine suppresses ventricular arrhythmia through blockade of Na+ -channels (Chang GJ et al., 1996). Note that the vascular and cardioprotective effects of liriodenine in ischemia–reperfusion injury involves NO-dependent pathway (Chang WL et al., 2004). Other properties: Atherosperminine from Fissistigma glaucescens inhibits the aggregation of platelets caused by adenosine-5-diphosphate, collagen and the platelet activating factor, and relaxes portions of rat thoracic aorta (Chen K et al., 1996). Another vasodilatating alkaloid characterized from the genus Fissistigma is (-)-discretamine (see Cyathostemma argenteum; Ko FN et al., 1994). Fissistigma lanuginosum elaborates a chalcone, pedicin, which inhibits the assembly of tubulin (IC50 = 300 mm; Alias Y et al., 1995).

Subclass Magnoliidae

17

References Alias Y, et al. (1995) J Nat Prod 58(8): 1160–1166. Chang GJ, et al. (1996) Br J Pharmacol 118(7): 1571–1583. Chang WL, et al. (2004) Nitric Oxide 11(4): 307–315. Chen K, et al. (1996) J Nat Prod 59(5): 531–534. Ko FN, et al. (1994) Br J Pharmacol 110(2): 882–888. Lin C, et al. (1993) Eur J Pharmacol 237(1): 109–116. Lin C, et al. (1994) Br J Pharmacol 113(1): 275–281.

Warning: Caution must be taken as the toxic effects of this plant are unknown. Goniothalamus macrophyllus (Bl.) Hook. f. & Thoms. [From Greek, gonia = hook, thalamus = receptacle, macro = large and phullon = leaves] Physical description: It is a treelet of the Common names: Bihidieng, rainforest of Indonesia, Malaysia and Thaipenawar hitam, bongsoi (Malay). land. Leaves: leathery and 25 cm–35 cm × 6 cm–11 cm. The blade is oblong-lanceolate, and shows 16 to 20 pairs of secondary nerves. The apex is acute or acuminate, and the base is sub-acute or round. The petiole is 2.5 cm long and stout. The flowers are solitary or in pairs, being green, large, slightly supraaxillary or pendulous from the branches below the leaves. The calyx consists of 3 sepals which are broadly ovate, acute, connate at the base and 1.5 cm long. The corolla comprises of 6 petals, the outer ones being oblong lanceolate, acute, 2.5 cm–3.75 cm long, and the inner ones half as long, ovate acuminate, and ciliate. The fruits are globular, ovoid and glabrous ripe carpels (Fig. 10). Pharmaceutical interest: Cytotoxic properties: Goniothalamus species are interesting because they produce cytotoxic acetogenins, styryllactones and quinones.

Fig. 10. Goniothalamus macrophyllus (Bl.) Hook. f. & Thoms.

18

Division MAGNOLIOPHYTA

Acetogenins: 2,4-cis and trans-giganterinones characterized from the bark of Goniothalamus giganteus Hook. f. & Thoms., inhibit the proliferation of the PC-human prostate adenocarcinoma cell-line cultured in vitro (Alali FQ et al., 1997).

Use: In Malaysia, a decoction of the root is used to aid abortion or to aid recovery from childbirth. A decoction of the leaves is drunk to combat fever. Indonesians drink a decoction of the roots for the same purpose.

OCH3

O

Goniothalamin

O

O

O

Kavain

Styryl lactones: An example of cytotoxic styryl-lactone is goniodiol-7monoacetate, which inhibits the proliferation of KB, P388, RPMI and TE 671 tumor cell-lines cultured in vitro (Wu YC et al., 1991). Another styryl-lactone, goniothalamin, characterized from Goniothalamus tapis Miq. inhibits the proliferation of HCG-27, MCF7, PAN C-1, HeLa cancerous cell-lines and noncancerous (3T3) cell-lines cultured in vitro (Ali AM et al., 1997). The cytotoxic mode of action involved here needs to be further clarified and could involve apoptosis, inhibition of the mitochondrial respiratory chain, and inhibition of topoisomerase II. Goniothalamin causes apoptosis in Jurkat T-cells on account of the activation of caspases 3 and 7 (Inayat-Hussain SH et al., 1999). Styryllactones characterized from Goniothalamus arvensis inhibit the mitochondrial respiratory chain (Peris E et al., 2000). Howiinol, a phenylethylene pyrone characterized from Goniothalamus howii exerts a potent inhibitory effect on cancer cells and inhibits topoisomerase II (Xu CX et al., 1999). 1-azaanthraquinones and 3-aminonaphthoquinone, 2 cytotoxic quinones were characterized from Goniothalamus marcanii (Soonthornchareonnon N et al., 1999). Other pharmacological properties: The abortifacient property of Goniothalamus macrophyllus (Bl.) Hook. f. & Thoms. could probably be owed to goniothalamin, the intraperitonneal injections of which (139 mg/Kg) during the first 7 days of gestation causes abortion in animals (Azimahtol HL et al., 1994). Goniothalamin and gonodiol inhibit the expression of intercellular and vascular inflammatory messengers by murine endothelial cells, suggesting anti-inflammatory and immunosuppressive properties (Tanaka S et al., 2001). Note that the structure of goniothalamin is very much like the structure of kawaine from Piper methysticum Forst. (family Piperaceae, order Piperales, subclass Magnoliidae), an anxiolytic herb of commercial value. Does Goniothalamus macrophyllus (Bl.) Hook. f. & Thoms. hold any anxiolytic properties?

Subclass Magnoliidae

19

References Alali FQ, et al. (1997) J Nat Prod 60(9): 929–933. Ali AM, et al. (1997) Planta Med 63(1): 81–83. Azimatol HLP, et al. (1994) Asia Pacific J Pharmacol 9(4): 273–277. Inayat-Hussain SH, et al. (1999) FEBS Lett 456(3): 379–383. Soonthornchareonnon N, et al. (1999) J Nat Prod 62(100): 1390–1394. Tanaka S, et al. (2001) Phytother Res 15(8): 681–686. Wu YC, et al. (1991) J Nat Prod 54(4): 1677–1081. Xu CX, et al. (1999) J Asian Nat Prod Res 2(1): 1–19.

Warning: Caution must be taken as the toxic effects of this plant are unknown. Mitrella kentii (Bl.) Miq. [From Greek, mitra = belt or girdle worn by warriors round the waist] Physical description: It is a woody climber of peat swamp forest, coastal beach and seashores of the AsiaPacific. The pedicels, calyx, outer petals and young leaves are covered with a golden tomentum. Leaves: simple, alternate and exstipulate. The petiole is 1 cm long. The blade is oblong-elliptic, leathery, dark green above and grey green below. The apex of the blade is acute-acuminate and the base is acute. The midrib is sunken above and raised below, and there are about 12 pairs of secondary nerves. The flowers are axillary. The calyx consists of a 3-angled connate cups, and the petals are ovate, valvate, small, the inner ones being smaller. The fruits are dull-orange ripe carpels (Fig. 11).

Synonymy: Melodorum pisocarpum Hk. f. et Thoms, Melodorum elegans Hk.f et Thoms. Common names: Kiawi (Indonesian).

Pharmaceutical interest: Dihydrochalcones: (-)-neolinderatin, (-)-lideratin Fig. 11. Mitrella kentii (Bl.) Miq. From: Herbarand 2 ,6 -dihydroxy-4 -methoxydihydro- ium 34155. Field collector & botanical identifichalcone, and (+)-catechin are known cation: JF Maxwell. Geographical localization: to occur in the stem bark of Mitrella ken- Singapore, 1982. tii (Bl.) Miq (Benosman A et al., 1997). One might set the hypothesis that these phenolic substances are responsible

20

Division MAGNOLIOPHYTA

for the property mentioned above by inhibition of enzymes that catalyze the synthesis of autacoids.

OH HO

O

HO

Uses: Malaysia: a decoction of the roots of Mitrella kentii (Bl.) Miq. is drunk to treat fever.

OH

HO

OH

OH OH

OH

O

OH

O

OH

(+) Catechin

(-) - Neolinderatin

(-) - Linderatin

Reference Benosman A, et al. (1997) J Nat Prod 60(9): 921–924.

Orophea polycarpa A. DC. [From Greek, orophe = roof, poly = many and karpos = fruit] Physical description: It is a tree of the rainforest of Malaysia which grows to a height of 8 m. The bark is blackish and fissured. The wood is yellow, and cross sections of stems show broad medullary rays. Leaves: simple, alternate and exstipulate.The petiole is indistinct. The blade is ovatelanceolate, and 5 cm × 2 cm–10 cm × 4 cm. The apex of the blade is attenuate and the base slightly cordate. The blade shows 7–10 pairs of indistinct secondary nerves. The inflorescences are terminal clusters of small and flesh colored flowers.The calyx consists of 3 valvate sepals which are smaller than outer petals. The corolla consists of 6 petals, the outer ones of which are shorter than the inner, and the inner petals joined at the top (in a roof-like manner). The andrecium consists of 6 stamens. The fruits are globose, 1 cm, bright red, and contain a single seed (Fig. 12).

Fig. 12. Orophea polycarpa A. DC. From: KLU 23448. Field collector and botanical identification: Benjamin Stone. Geographical localization: Gua Musang, Kelantan, Malaysia, 1976.

Subclass Magnoliidae O

21

O

HO

HO NH

H3CO

NH H3CO

OCH3 OCH3 Enterocarpam I

OCH3 Enterocarpam II

Pharmaceutical interest: The anti-inflaSynonymy: Orophea gracilis King. mmatory property of Orophea polycarpa A. DC is still not confirmed yet. Uses: In Malaysia, Orophea polyA dichloromethane extract of leaves carpa A. DC. is used to promote the of Orophea enneandra displays antisecretion of sweat and to soothe an fungal, antioxidant and radical scavinflamed throat. enging properties on account of lignans: (-)-phylligenin, (-)-eudesmin, (-)epieudesmine, tocopherol derivative: polycerasoidol and a polyacetylene: oropheic acid (Cavin A et al., 1998). Aristolactams: enterocarpam I and II are known to occur in Orophea enterocarpa (Kamalia M et al., 1986). Enterocarpam II has been synthesized (Couture A et al., 1998). References Cavin A, et al. (1998) J Nat Prod 61(12): 1497–1501. Couture A, et al. (1998) J Org Chem 63: 3128–3132. Kamalia M, et al. (1986) Phytochem 25(4): 965–967.

Warning: Caution must be taken as the toxic effects of this plant are unknown. Polyalthia cauliflora Hook. f. & Thoms. var. beccarii (King) J. Sinclair [From Greek, polus = many, althein = cure, from Latin, caulis = stem and floris = flower] Physical description: It is a shrub of the Synonymy: Balet (Malay). rainforests of Borneo, Malaysia and Sumatra. Leaves: simple, alternate and exstipulate. The blade is 9 cm–20 cm × 4 cm–8 cm, leathery, glossy, elliptic acuminate, acute at the base and shows 8–10 pairs of secondary nerves. The petiole is 5 mm– 7 mm long. The flowers are cauline, on 2 cm–4 cm long pedicels. The calyx

22

Division MAGNOLIOPHYTA

consists of 3 sepals which are triangular, pubescent on the outside and 6 mm–7 mm long. The corolla consists of 6 petals arranged in 2 whorls. The petals are 3.5 cm–5.5 cm long, thick, and cream to pinkish brown. The fruits consist of several ovoid, 1 cm long, ripe, 2 cm–2.5 cm long carpels, each carpel containing 1 to 2 seeds (Fig. 13). Uses: Polyalthia cauliflora Hook. f. & Thoms. var. beccarii (King) J. Sinclair is principally used in Malaysia, where a paste of the powdered leaves is applied externally to treat skin infection.

Pharmaceutical interest: The antiseptic property of Polyalthia cauliflora Hook. f. & Thoms. var. beccarii (King) J. Sinclair involves probably four sorts of Fig. 13. Polyalthia cauliflora Hook. f. & Thoms. natural products: terpenes, alkaloids, var. beccarii (King) J. Sinclair. benzopyrans and tannins: Diterpenes: A common and interesting feature of Polyalthia species, is the presence of cytotoxic and antimicrobial clerodane and labdane diterpenes. Labdane diterpenes characterized from Polyalthia barnesii inhibit the proliferation of several human cancer cell-lines and P388 cell-line cultured in vitro (ED50 = 0.5 µg/mL–18.5 µg/mL; Ma X et al., 1994). Polyalthialdoic acid, a clerodane diterpene characterized from the stem bark of Polyalthia longifolia, inhibits the proliferation of human tumor cell-lines cultured in vitro (ED50 = 0.6 µg/mL; Zhao GX et al., 1991). The stem bark of Polyalthia longifolia var. pendulla contains a number of clerodane diterpenes which are strongly antimicrobial (minimal inhibiting concentration: 8 µg/mL–64 µg/mL; Rashid MA et al., 1996). Other examples of terpenes are leishmaniacidal (Leishmania donovani donovani ED50 = 0.75 mg/mL) labdane diterpenes characterized from the stem bark Polyalthia macropoda (Richomme P et al., 1991) and a lanostanetype triterpene from Polyalthia suberosa (Roxb.). Twaites which inhibits the replication of the Human Immunodeficiency Virus in H9 lymphocytes (Li H et al., 1993). Isoquinoline alkaloids: Lanuginosine and oxostepharine characterized from the bark of Polyalthia longifolia var. pendulla, inhibit, in vitro, the proliferation of

Subclass Magnoliidae

23

O OH

OH

O

N

CH3

OH

Clerodane

Labdane

Oliveroline

Staphylococcus aureus. Lanuginosine inhibits the proliferation of several types of fungi (Ferdous AJ et al., 1992).The stem bark of Polyalthia longifolia contains liriodenine, which is cytotoxic (WuYC et al., 1990; see Fissistigma species).The leaves Polyalthia oliveri contain oliveroline, which interestingly displays, in vivo, anti-Parkinson properties, whereas oliverine relaxes vascular smooth muscle in a papaverine-like way and is therefore antihypertensive (Quevauviller A et al., 1977). Benzopyrans: Polyalthidine characterized from Polyalthia cerasoides inhibits the enzymatic activity of mitochondrial ubiquinol cytochrome-C oxido reductase respiratory chain in cancer cell-line cultured in vitro (IC50 < 5 mM; ZafraPolo MC et al., 1996). References Ferdous AJ, et al. (1992) Fitoter 63(6): 549–550. Li H, et al. (1993) J Nat Prod 56(7): 1130–1133. Ma X, et al. (1994) Phytochem 37(6): 1659–1662. Quevauviller A, et al. (1977) CR Acad Sci Hebd Sceances Acad Sci D 284(1): 93–96. Rashuid MA, et al. (1996) Phytother Res 40(1): 79. Richomme P, et al. (1991) Planta Med 57(6): 552–554. Zafra-Polo MC, et al. (1996) J Nat Prod 59(10): 913–916. Zhao GX, et al. (1991) Planta Med 57(4): 380–383. Wu YC, et al. (1990) J Nat Prod 53(5): 1327–1336.

Warning: Caution must be taken as the toxic effects of this plant are unknown. Pyramidanthe prismatica J. Sinclair (Hook. f. & Thoms.) [From Greek, puramis = pyramid and prisma-matos = thing sawn] Physical description: It is a climber of the rainforest of Malaysia which grows from tree to tree to a length of 12 m. The bark is blackish and showily lenticelled.

Synonymy: Fissistigma cylindricum (Maingay) Merr., Melodorum prismaticum Hk. f. & Thoms.

24

Division MAGNOLIOPHYTA

Uses: In Malaysia, a decoction of the roots of Pyramidanthe prismatica (Hook. f. & Thoms.) J. Sinclair is drunk to treat diarrhea and snake bites. The pharmacological property of this plant is unknown. The plant may have disappeared before it is assessed for pharmacology.

Leaves: simple, alternate and exstipulate. The petiole is stout, 1 cm long and channeled. The blade is leathery, 14 cm–20 cm × 5 cm–7 cm, dark green on the surface, glossy and velvety underneath. The apex is shortly Fig. 14. Pyramidanthe prismatica (Hook. f. acuminate or acute and the base is & Thoms.) J Sinclair. From: KLU Herbarium round. The blade shows 12–14 pairs 042520 and 15681 Field collector & botanical identification: Ahmad, Singapore, 1977. of secondary nerves with conspicuous internerves. The flower buds are axillary, golden velvety, 5 cm–7 cm long and conical. The calyx is disc-shaped, obscurely 3-angled and persistent in fruits. The petals are valvate, linearlanceolate, the outer ones are 5 cm–7 cm long, and the inner one are ovate and 1 cm long. The stigmas are capitate and lobed. The fruits are ovoid, 2 cm × 1.5 cm, dark green and rugose (Fig. 14). Warning: Caution must be taken as the toxic effects of this plant are unknown. Uvaria grandiflora Roxb. [From Latin, grandis = full-grown and flores = flower] Physical description: It is a climbing Synonymy: Uvaria purpurea Bl. rainforest shrub found in Burma, Thailand, Common names: Pisang pisang Indonesia, Malaysia and the Philippines. (Malay). The young stems are hairy. Leaves: simple, alternate and exstipulate. The blade is 11 cm–28 cm × 6 cm–10 cm, thin, dark green, glossy on the surface and hairy below and shows 14–17 pairs of secondary nerves. The petiole is 3 mm–7 mm long and hairy. The flowers are solitary, facing the leaves and 9 cm–11 cm long. The calyx consists of 3 sepals which are 2 cm–2.5 cm long, thin, yellowish brown and broadly triangular. The corolla consists of 6 petals which are 3.5 cm–4 cm long, oblong cylindrical and red-purplish. The fruits are 4 cm–6 cm long and hairy ripe carpels containing 2 series of glossy seeds (Fig. 15).

Subclass Magnoliidae

25

Uses: In Malaysia, the leaves of Uvaria grandiflora Roxb. are cooked and ingested to treat flatulence, and a decoction is drunk to assuage stomachache and to aid in recovery from childbirth. The pounded leaves are used to counteract putrefaction.

Pharmaceutical interest: Chemotherapeutic properties: Acetogenins: Uvarigrin, an acetogenin characterized from the roots of Uvaria grandiflora Roxb, inhibits the growth of HCT-8, BeI7402 and A2780 human tumor cells with ED50 of 0.15 µg/mL, Fig. 15. Uvaria grandiflora Roxb. From: KLU 0.21 µg/mL and 0.41 µg/mL respec- 037294. Field Collector: SC Chin & Mustafa, tively (Pan XP et al., 1997). A num- 4 Feb 1985. Geographical localization: Sungai ber of triterpenes (glutinol, glutinone, Layang, in old rubber estate, Negeri Sembilan, Malaysia. taraxerol, β-sitosterol) and acetogenins (uvariamicin I–III, squamocin, squamocin-28-one, narumicin I–II, isodesacetyluvaricin and panalicin) characterized from Uvaria narum and Uvaria hookeri inhibit the proliferation of several sorts of microorganisms including cocci: Staphylococcus pyogene; bacilli: Bacillus brevis, Bacillus circulans, Bacillus licheniformis, Salmonella thyphi, Escherichia coli, Klebsiella aerogene, Pseudomonas pyocyaneae; and fungi: Aspergillus niger, Penicillium notatum, Trichophyton mentagrophytes, Microsporum gipsum, Epidermophyton floccosum. A number of these acetogenins destroy Haemonchus contortus as efficiently as a mebendazole (Vermox® ; Padmaja V et al., 1993). Root bark extracts of Uvaria narum and Uvaria hookeri are cytotoxic on probable account of acetogenins (Padjama V et al., 1995). The essential oil extracted from the root bark of Uvaria narum is calming, stops flatulence and counteracts putrefaction. This oil contains 15% of bornyl acetate, 8% of patchoulinone and a tricyclic sesquiterpene ketone. Flavonoids: An interesting feature of the Uvaria species is the occurrence of C-benzylated flavonoids such as uvaretin and isouvaretin characterized from Uvaria chamae (Hufford CD et al., 1976; 1978), or triuvaretin and isotriuvaretin,

H

HO

Taraxerol

26

Division MAGNOLIOPHYTA

characterized from the root bark of Uvaria leptocladon (Nkunya MHH et al., 1993). Extracts of the bark of Uvaria lucida and the root bark of Uvaria scheffleri destroy efficiently the multidrug-resistant K1 strain of Plasmodium falciparum on account of uvaretin (IC50 = 3.49 µg/mL) and diuvaretin (IC50 = 4.2 µg/mL; Nkunya MH et al., 1991). Hamiltrone, an aurone characterized from Uvaria hamiltonii, has a strong DNA strand-scission property (Huang L et al., 1998). Chamuvaretin, a dihydrobenzylchalcone from Uvaria chamae, induces mutations in TA98 and TA 100 strains Salmonella thyphimurium (Uwaifo AO et al., 1979). HO

HO

N

H3CO HO

CH3

OH

H3CO O Uvaretin

OH Boldine

Isoquinoline alkaloids: An ethanolic extract of the root bark of Uvaria chamae relaxes the smooth muscles of guinea-pig ileum, rabbit jejunum and rat uterus in vitro and in vivo (Langason RBF et al., 1994), and displays anti-ulcerogen, hepatoprotective and trypanocidal properties (Madubunyi II et al., 1996). The antispasmodic property could be attributed to toisoquinolines alkaloid which are known to block the muscarinic receptors (see Fissistigma), whereas the hepatoprotective property could involve choleretic aporphinoid boldine-like alkaloids. Boldine is commercially used to treat hepatic disturbances and is currently extracted from Peumus boldus (family Monimiaceae). Boldine is found in a number of plants classified within the genus Desmos which botanically is close to the genus Uvaria. References Huang L, et al. (1998) J Nat Prod 61(4): 446–450. Hufford CD, et al. (1976) J Org Chem 41(7): 1297–1298. Hufford CD, et al. (1978) Lloydia 41(2): 156–160. Langason RBF, et al. (1996) Fitoter 65(3): 235–240. Madubunuyi IJ, et al. (1996) Int J Pharmacog 34(1): 34–40. Nkunya MHH, et al. (1993) Phytochem 32(5): 1297–1300. Padmaja V, et al. (1993) J Ethnopharmacol 40(3): 181–186. Padmaja V, et al. (1995) Fitoter 66(1): 77–81. Pan XP, et al. (1997) Yao Xue Xue Bao 32(4): 286–293. Uwaifo AO, et al. (1979) Cancer Lett 8(1): 87–92.

Warning: Caution must be taken as the toxic effects of this plant are unknown.

Subclass Magnoliidae

27

3. Family MYRISTICACEAE R. Brown 1810 nom. conserv., the Nutmeg Family Physical description: The family Myristicaceae consists of about 16 genera and 380 species of lowland rainforest trees. In this family, isoquinolines and acetogenins weapons are replaced by phenylacylphenols, serotonine-like indole alkaloids and lignans. Myristicaceae are quite easily recognized in the fields as they have a straight trunk which exudes a very characteristic bloodlike sap, few leaves (hence a Christmas tree look) and nutmeg-like fruits. The leaves are simple, without stipules and alternate, often dark green and leathery. The flowers are tiny, male or female, and on different trees. The perianth is tiny, cup-shaped and 3-lobed. The stamens are united in a column, and the ovary is 1-celled and contains 1 ovule. The fruits are yellowish-red, ovoid, drupes, the seed of which is embedded in an aril, the divisions of which are of taxonomic importance. Pharmaceutical interest: The family Myristicaceae is interesting because it produces indole alkaloids which bind to serotonine receptors and hence have some potential for the treatment of anxiety, mood disorders and other psychological disturbances. Such alkaloids are N,N-dimethyl tryptamine, 5-methoxyN,N-dimethyl tryptamine, 2-methyl-1,2,3,4-tetrahydro-β-carboline which have been characterized from Virola sebifera which is used by South American shamans to cause hallucination (Fig. 14). Other interesting compounds are possible cytotoxic, antinematodal and antibacterial phenylacylphenols known as iryantherins which are very specific to the genus Iryanthera. A classical example of Myristicaceae is Myristica fragrans Houtt., the dried seeds of which: nutmeg are flavorful, narHO NH2 cotic and carminative. Excessive ingestion of nutmeg causes H3 CO tachycardia, early constriction O O of the pupils, and a divorce from HO OH surroundings, delirium, semisNoradrenaline Myristicin tupor and an “unpleasant and frightening” experience”. The CH3 N

HO

OCH3

OCH3

HO

HO

N H

OH

O

OH Iryantherin A

NH2

CH3

5-Hydroxy-N, N-dimethyl tryptamine

N H Serotonine

Fig. 16. Examples of neuroactive natural products characterized from the family Myristicaceae. Similitude of chemical structure with noradrenaline and serotonine.

28

Division MAGNOLIOPHYTA

neuroactive principles involved are phenylpropanoids: myristicin and elemicin, the chemical structures of which are similar to the chemical structure of noradrenaline (Fig. 16). In the Asia-Pacific, about 20 species of plants classified within the family Myristicaceae are used for medicinal purposes, mostly for gastrointestinal disturbances. Horsfieldia irya (Gaertn.) Warb. [After Thomas Horsfield (1773–1859), an American doctor and botanist who took service in the Dutch East Indies] Fig. 16. (a) Horsfieldia irya (Gaertn.) Warb.

Physical description: It is a mediumsized tree found in the swampy rainforests of the Asia-Pacific. The bark Synonymy: Horsfieldia lemmania (A. shows diamond-shaped short fissures DC.) Warb. and exudes a red sap after cutting. Common name: Penarahan pianggu Leaves: simple, alternate and exstip(Malay). ulate. The blade is oblong-lanceolate, 14 cm–20 cm × 4 cm–5 cm, and shows 10–20 pairs of arching secondary nerves. The flowers are tiny with a bilobed perianth cup. The fruits are globose, dehiscent, yellowish-red and 1.5 cm × 1 cm drupes. The seed is embedded in a non-divided aril [Fig. 16(a)]. Pharmaceutical interest: Nothing is Uses: In China, the red sap of Horsknown so far about the pharmacofieldia irya (Gaertn.) Warb. is used logical properties of Horsfieldia irya to soothe sore throat. In Malaysia, (Gaertn.). Note that the plant is known a decoction of the bark is used to to elaborate 5,7-Dihydroxychromones soothe sore throat. and 8-hydroxytetrahydrochromones which might have anti-inflammatory properties but this remains to be confirmed experimentally. The fruit of Horsfieldia amygdaline contains a chroman which dosedependently and competitively inhibits the enzymatic activity of phospholipase A2 of rabbit platelets, with an IC50 value of 6.7 mM (Miyake A et al., 1992). Methanolic extracts of leaves, roots and the stem bark of Horsfieldia helwigii show a broad spectrum of antibacterial activity (Khan MR et al., 2001).

Subclass Magnoliidae

29

References Gonzales MJ, et al. (2002) Phytochem 61(8): 995–998. Khan MR, et al. (2001) Fitoter 72(4): 423–427. Mikaye A, et al. (1992) J Pharmacol Exp Ther 263(3): 1302–1307.

Warning: Caution must be taken as the toxic effects of this plant are unknown. Knema globularia (Lamk.) Warb. [From Greek, knema = internode and from Latin, globulus = globe] Physical description: It is a treelet Synonymy: Knema corticosa Lour., found in the Asia-Pacific and China Myristica glaucescens, Knema (Yunnan). The stems are scurfy. Leaves: missioni (King.) Warb., Knema simple, alternate and exstipulate. The sphaerula (Hk. f.). blade is narrow, slightly glaucous Common names: Seashore below and scurfy, glossy dark green nutmeg, small-leaved nutmeg. on the surface, lanceolate, and 7 cm–15 cm × 1.5 cm–5 cm. The apex Uses: In Vietnam, the oil expressed and base of the blade are both pointed, from the seeds of Knema globularia and the blade shows 12–20 pairs of sec(Lamk.) Warb. is applied externally ondary nerves. The flowers are tiny. The to counteract putrefaction. fruits are globular, succulent and orange drupes which are at first scurfy, and exhibit a perianth scar at the apex. The seed is embedded in a red aril divided only at the apex (Fig. 17). Pharmaceutical interest: The therapeutic potential of Knema globularia (Lamk.) Warb. is unexplored but one could suspect its antiseptic activity to be mediated by phenolic compounds, since phenylacylphenolic compounds: kneracheline A and B, characterized from Knema furfuracea inhibit the proliferation of bacteria cultured in vitro (Zahir LA et al., 1994). Phenolic compounds characterized from the stem bark of Knema glomerata inhibit moderately the proliferation of human tumour cell-lines cultured in vitro (Zeng L et al., 1994). 3-Undecylphenol and 3-(8Z-tridecenyl)-phenol characterized from Knema hookeriana inhibit the proliferation of Bursaphelechus

Fig. 17. Knema globularia (Lamk.) Warb. From: KLU Herbarium 11926. Field collector & botanical identification: Benjamin C Stone, 24 May 1974. Geographical localization: Pulau Tioman, NR Kg Tekek, along Sg. Ayer Besar, Malaysia.

30

Division MAGNOLIOPHYTA

xylophilus cultured in vitro with a maximum effective dose of 4.5 mg/cotton ball and 20 mg/cotton ball respectively (Alen Y et al., 2002). References Alen Y, et al. (2002) Z Naturforsch 55(3–4): 300–303. Zahir A, et al. (1994) J Nat Prod 56(9): 1634–1637. Zeng L, et al. (1994) J Nat Prod 57(3): 376–381.

Warning: Caution must be taken as the toxic effects of this plant are unknown. Myristica iners Bl. [From Greek, muron = a sweet juice distilled from plants and from Latin, iners = soft] Physical description: It is a timber tree found in Malaysia, Indonesia, Vietnam, Thailand and Burma. The wood is of good quality, red and exploited for commercial purposes. The bark is black and fissured and exudes a blood-like sap when cut. Leaves: simple, alternate and exstipulate. The blade is papery, oblong, lanceolate, and 12 cm–20 cm×5 cm–6 cm. The blade is tapering at the base and the apex and shows 12–15 pairs of secondary nerves. The margin is slightly recurved. The fruits are ovoid, pale yellow, and 5 cm long drupes. The seed is embedded in a finely divided red aril (Fig. 18). Common names: Laka (Malay). Uses: Malays have been known to burn the wood of this tree as incense. In Indonesia, the sap of Myristica iners Bl. is drunk to promote urination. The therapeutic potential of Myristica iners Bl. is unknown but one might set the hypothesis that cytotoxic or antiviral lignans could be characterized from it as several lignans are known to occur in Myristica argentea Warb. (Filleur F et al., 2002).

Fig. 18. Myristica iners Bl.

Subclass Magnoliidae

31

Reference Filleur F, et al. (2002) Nat Prod Lett 16(1): 1–7.

Warning: Caution must be taken with these plants as their toxic effects are unknown. B. Order LAURALES Lindley 1833 The order Laurales consists of 8 families and about 2500 species of woody plants which are thought to have evolved from the order Magnoliales from which it inherits the capability to elaborate isoquinoline alkaloids (benzylisoquinolines or aporphines), phenylpropanoids and essential oils.

1. Family LAURACEAE A. L. de Jussieu 1789 nom. conserv., the Laurel Family Physical description: The family Lauraceae is by far the largest family of the order Laurales with about 50 genera and 2000 species of trees shrubs and herbs producing benzylisoquinoline and oxoaporphine alkaloids, phenylpropanoids (safrole), lignans, terpenes (mono- and sesquiterpenes), and mucilage. The bark of Lauraceae is smooth, leathery, and lenticelled. The inner bark is fragrant, yellow, orange, reddish or pinkish and exudes a pale yellow to pale brown sap after incision. The leaves in this family are simple, without stipules, opposite, spiral, whorled or alternate, usually with several gland dots and often aromatic when crushed. The inflorescences are racemose or in clusters. The flowers are bisexual, actinomorphic, small, regular, greenish-white or yellow, fragrant, trimerous (2 rows of 3 tepals) and variO HO ously accrescent in fruit. The stamens are O HO typically in 4 whorls. The gynecium consists of a carpel forming a single-celled and superior ovary. The style is terminal and simple, and the stigma is small. The HO fruits are baccate or drupaceous, and often NH2 seated or enclosed in a persistent and cupshaped corolla, the morphology of which is Safrole Noradrenaline of taxonomic value.

32

Division MAGNOLIOPHYTA

Pharmaceutical interest: Classical examples of Lauraceae are Laurus nobilis L. (sweet bay laurel), Cinnamomum zeylanicum Nees (cinnamon), Cinnamomum camphora (L.) T. Nees & Eberm. (camphor), Persea americana Miller (avocado), Sassafras albidum (Nutt.) Nees (sassafras oil), Umbellularia californica (California bay laurel), Persea nanmu Oliv. (nan-mu wood), Nectandra rodiaei Schk. (green-heart wood), Eusideroxylon zwageri (ironwood) and Ocotea bullata E. Mey.The dried ripe berries of Laurus nobilis L. (Lauri Fructus; Swiss Pharmacopoeia 1934) containing about 1% of volatile oil and 25% of fixed oil were used to promote digestion, menstruation and urination. Safrole is a neuroactive because its chemical structure is similar to the chemical structure of asarone, myristicine and noradrenaline. Safrole is aromatic and used to give flavor in root beer. At concentration levels of 0.5% and 1% of the diet, safrole causes liver tumors in rats. It is found in camphor oil, in oil of cinnamon, and especially in sassafras. This family is interesting because the alkaloids it produces are cytotoxic and neuroactive. In the Asia-Pacific, about 150 species of plants classified within the family Lauraceae are used for medicinal purposes, and especially to treat digestive ailments and to invigorate. Cassytha filiformis L. [From Latin, filum = thread and forma = shape] Physical description: It is a slender, tropical, parasitic plant which grows by the seashores of the Asia-Pacific. The plant scrambles over bushes and trees. The stems are pale green, succulent, soft, thread-shaped and without leaves. The flowers are 2 mm–3 mm long, white, yellowish, and globose. The corolla consists of 6 sepals, where the 3 outer ones are smaller than the inner ones. There are 9 or 6 stamens, in 3 whorls, and the ovary is superior. The fruits are berries of about 5 mm diameter and enclosed in an enlarged, succulent, pale and persistent corolla (Fig. 19). Pharmaceutical interest: Sympatholytic properties: Cassytha filiformis L. contains ocoteine, an aporphine alkaloid which blocks competitively α1 -adrenoreceptors of rat thoracic aorta. At high concentration, this alkaloid blocks 5-hydroxytryptaminergic receptors and acts Fig. 19. Cassytha filiformis L. on ventricular myocytes (Chang CW et al., 1997).

Subclass Magnoliidae

33

Common names: Dodder-laurel, snotty-gobble, chemar batu (Malay). Uses: In Malaysia, a lotion consisting of powdered Cassytha filiformis L. and sesame oil is used externally to stimulate hair growth. In Indonesia, Cassytha filiformis L. is used to expel intestinal worms, and it is combined with nutmeg in order to assuage stomach and bowel discomfort. In the Philippines, a decoction of the fresh plant is drunk to induce parturition and to stop haemoptysis. In Taiwan, the stems are used to promote urination, to treat gonorrhea and to assuage kidney discomfort. In Vietnam, the plant is used to expel impurities, to treat syphilis and to treat pulmonary diseases.

Fig. 20. Hypothetical pharmacological properties Cassythia filiformis L alkaloids: the blockade of α1 -adrenoreceptors stimulates urination through relaxation of the trigone (T), ureter (UR) and sphincter (S). Blockade of α1 -adrenoreceptors stimulates hair growth through relaxation of hair follicles, smooth muscle and scalp vessels. Contraction of uterus through prostaglandin. F2α .

Physiological stimulation of α1 -adrenoreceptors contracts the smooth muscle of arteries, veins, splenic capsules, uterus, vas deferent, prostatic capsules, iris radial muscles (mydriasis), trigone and sphincter of the urinary bladder, ureter, hair follicles, and increases gland secretion.

An example of α1 -adrenoreceptor blocker is prazosin OCH3 which is currently used to reduce blood pressure. O This drug preserves pre-junctionnal α2 -receptors function and prevents an unmodulated disproporN O CH3 tionate increase in noradrenaline release with sympathic activation. The α1 -adrenoreceptor antagonist property of ocoteine and probably of other isoquinoline analogues, could explain some of the medicinal H3CO uses mentioned above (Fig. 20). The hair tonic propOCH3 erty of Cassythia filiformis L could be mediated via Ocoteine a blockade of α1 -adrenergic receptors of the hair follicles, and vasodilatation of the vessels that irrigate the scalp. Minoxidil is a vasodilator is used to stimulate hair growth.The diuretic use of Cassytha filiformis L. may involve relaxation of the trigone, sphincter and ureter. The parturition-inducing property of Cassythia filiformis L. does not

34

Division MAGNOLIOPHYTA

result from α1 -adrenoreceptors blockade but probably from prostaglandin.F2α through the activation of phospholipase A2 or cyclo-oxygenase. Prostaglandin F2α contracts the uterus and is used in veterinary medicine to cause abortion. This phospholipase A2 -or cyclo-oxygenase-mediated mechanism may explain the fact that ocoteine inhibits the aggregation of platelets (Chang FR et al., 1998). This plant elaborates a number of cytotoxic aporphine alkaloids such as neolitsine, cassythine and actinodaphnine. Neolitsine alleviates HeLa and 3T3 cells (IC50 : 21.6 µM, and 21.4 µM, respectively), and cassythine and actinodaphnine are active against Mel-5 (IC50 : 24.3 µM and 25.7 µM, respectively) and HL-60 (IC 50: 19.9 µM and 15.4 µM, respectively)(Stevigny C et al., 2002). References Chang FR, et al. (1998) J Nat Prod 61(7): 863–866. Chang CW, et al. (1998) Jpn J Pharmacol 73(3): 207–214. Stevigny C, et al. (2002) Planta Med 68(11): 1042–1044.

Warning: Caution must be taken as the toxic effects of this plant are unknown. Cinnamomum iners Reinw. ex Bl. [From Greek, kinnamon = cinnamon and from Latin, iners = soft] Physical description: Cinnamomum Common names: Clove cinnamon, iners Reinw. ex Bl. is a tree which grows wild cinnamon; kulit kayu manis to a height of 24 m and a girth of 1.8 m. (Malay). The plant is found in India, Indo-China, Indonesia, the Philippines, Peninsular Malaysia in lowland and hill forests, or planted in towns as a shade tree. The wood is of commercial value. The bark is greyish-brown, smooth and lenticelled. The inner bark is pinkish and fragrant. The sapwood is whitish. Leaves: fragrant, simple, opposite and exstipulate.The petiole is 1 cm–2 cm long and yellowish. The blade is leathery, oblong-elliptic, glaucous below and 7.5 cm–30 cm×2.5 cm–9 cm.The apex of the blade is blunt and the base is cuneate. The blade shows 3 yellowish longitudinal nerves with scalariform tertiary nerves. Inflorescence: axillary or terminal, 10 cm–20 cm long light green panicles. The flowers are tiny, whitish, and smelly. The fruits are ovoid, green, glossy, and 1.5 cm × 1 cm drupes on persistent corolla cups (Fig. 21). Pharmaceutical interest: The pharmacological potential of Cinnamomum iners Reinw. ex Bl. would be worth studying, as interesting findings were made in other Cinnamomum species such as Cinnamomum cassia. One such finding is that trans-cinnamaldehyde from Cinnamomum cassia inhibits in vitro

Subclass Magnoliidae

35

Uses: In Indonesia, an extract of the bark is drunk to aid recovery from childbirth and Malays drink a decoction of the roots for the same purpose. In Malaysia, a poultice made from the powdered leaves is applied externally to assuage the pain caused by rheumatism. In Vietnam, the bark is used to treat colic and to relieve the bowels of costiveness.

O H Fig. 21. Cinnamomum iners Bl.

Trans - cinnamaldehyde

the activity of aldose reductase and nitric oxide synthetase with an IC50 value of 0.003 mg/mL and about 1µg/µL respectively (Lee HS 2002; Lee HS et al., 2002a). Nitric oxide is a toxic-free radical that can cause substantial tissue damage in high concentrations, especially in the brain. In a stroke, for example, large amounts of nitric oxide are released from nerve cells to cause damage to surrounding tissues. Therefore, one might set the hypothesis that the medicinal properties mentioned above involve the reduction of nitric oxide levels in inflamed tissues by cinnamic acid derivatives which are also antiseptic and antimicrobial. These cinnamates are possibly involved in the dose-dependent anti-nociceptive effects displayed by an ethanolic extract of Cinnamomum zeylanicum against both acetic acid-induced writhing and hot plate-induced thermal stimulation. (Attah AH et al., 1998). References Attah AH, et al. (1998) J Ethnopharmacol 60(2): 117–124. Lee HS. (2002) J Pharm Pharm Sci 5(3): 226–230. Lee HS. (2002a) J Agric Food Chem 50(26): 7700–7703. Westra WH, et al. (1998) Head Neck 20(5): 430–433.

Warning: Squamous cell carcinoma of the tongue associated with cinnamon gum use is reported (Westra WH et al., 1998).

36

Division MAGNOLIOPHYTA

Litsea glutinosa (Lour.) C.BV. Robinson [From Chinese, litse = Litsea glutinosa (Lour.) C. BV. Robinson and from Latin, glutinis = glue] Physical description: Litsea glutinosa (Lour.) Synonymy: Litsea chinensis C.BV. Robinson is a tropical tree, which grows Lam., Litsea sebifera Pers. to a size of 15 m by 90 cm, that is native to Common name: Indian laurel, tropical Asia. The young stems are tomenpond spice. tose and yellowish. Leaves: simple, stipulate and smelly. The blade is 7 cm–16 cm × 3.5 cm–8 cm, elliptic-oblong, glaucous and yellowish, hairy underneath, hairy on midrib and shows 8–10 pairs of secondary nerves. The apex of the blade is blunt and the base is cuneate. The inflorescences are axillary and 7 mm long umbellules. The fruits are globose, black, glossy and large drupes of 2.5 cm in diameter, obconic, succulent and persistant corolla cups (Fig. 22). Pharmaceutical interest: Antibacterial and antiviral properties: A methanolic extract of the bark of Litsea glutinosa (Lour.) C.BV. Robinson inhibits the growth of 16 microorganisms as effectively as chloramphenicol (Mandal SC et al., 2002). This plant produces a eudesman sesquiterpene called verticillatol and the lignan (+)demethoxyeoiexcelsin which inhibit the replication of the Human Immunodeficiency Virus with IC50 of 34.5 mg/mL and 16.4 mg/mL respectively (Hoang VD et al., 2002). Other properties: The essential oil extracted from Litsea glutinosa (Lour.) C. BV. Robinson displays a number of psychopharmacological

Fig. 22. Litsea glutinosa (Lour.) C. BV. Robinson.

Uses: In Burma, Litsea glutinosa (Lour.) C. BV. Robinson is used to stop dysentery. In China, the pounded leaves are applied externally to treat skin diseases. In Malaysia, the crushed seeds are applied externally to treat skin diseases. In the Philippines, Litsea glutinosa (Lour.) C. BV. Robinson is used to stop dysentery. The roots and leaves are used to soothe sprains and bruises. In Vietnam, the pounded bark is used to heal boils.

Subclass Magnoliidae

37

O O H

H

OH O

O

O

O OH

Verticillatol

OCH3

Demethoxyeoiexcelsin

(Menon MK et al., 1970) and cardiovascular (Kar A et al., 1970) properties experimentally. References Hoang VD, et al. (2002) Phytochem 59(3): 325–329. Kar A, et al. (1970) Indian J Exp Biol 8(1): 61–62. Mandal C, et al. (2000) Fitoter 71(4): 439–441. Menon MK, et al. (1970) Indian J Physiol Pharmacol 14(3): 185–192.

Warning: Caution must be taken as the toxic effects of this plant are unknown.

C. Order PIPERALES Lindley 1833 The order Piperales consists of 3 families and about 2000 species of herbs, shrubs and trees which are thought to have originated directly from Magnoliales from which are inherited the ability to elaborate piperidine, isoquinoline and phenanthrene alkaloids, essential oils, triterpenes and lignans (Appendix I). Piperales can be quickly recognized in a field collection by their strongly articulate stems. Piperales of economic importance are so far found in the family Piperaceae which provides pepper and kava.

1. Family CHLORANTHACEAE R. Brown ex Lindley 1821 nom. conserv., the Chloranthus Family Physical description: The family Chloranthaceae comprises of 5 genera and about 75 species of tropical and subtropical herbs which have been hardly studied from a pharmaceutical point of view. In terms of evolution, this family probably connects the order Piperales to the order Magnoliales. The leaves are simple, opposite, lobed or entire, stipulate and with a petiole more or less connate. The flowers are tiny, unisexual or bisexual, and epigynous and arranged in axillary or terminal compound spikes, panicles or heads.

38

Division MAGNOLIOPHYTA

The perianth is wanting or moderately 3-lobed. The andrecium consists of 1–3 stamens connate into a mass. The anthers are1–2-celled, and open lengthwise. The gynecium comprises of a single carpel. The stigma is sessile, the style is short, and the ovule is solitary and orthotropous. The fruits are small, and ovoid or globose berries. Pharmaceutical interest: Chloranthaceae are interesting because they produce pentacyclic triterpenes such as betulinic acid. Chloranthus officinalis Bl. Chloranthus eliator R. Br. ex Link (Chloranthus officinalis Bl.), Chloranthus spicatus (Thunb.) Mak. (Chloranthus inconspicuus Sw.), Chloranthus serratus, Chloranthus oldhamii Solms, Sarcandra glabra (Thunb.) Nak., Ascarina maheshwarii Swamy are of medicinal value in the Asia-Pacific. These are often used to make aromatic teas, treat fever and to invigorate health. It will be interesting to learn whether more intensive future research on this family will disclose any molecules of therapeutic interest. Chloranthus eliator R. Br. ex Link

Synonymy: Chloranthus officinalis Bl.

[From Greek, khloros ´ = green and anthos = flower]

Common names: Chloranthus, sigeh putih, sambau paya (Malay).

Physical description: It is an understorey herb which grows to a height of 60 cm in the rainforest of tropical Asia. Leaves: simple, opposite, aromatic, serrate, elliptic, lanceolate, acuminate, dark green, glossy, and very thin. The blade is 15 cm × 6 cm. The petiole is 5 mm long and the stipules are small on the margin of the petiole sheath. The inflorescences are terminal groups of 4 or 5, 4 cm long spikes. The flowers are tiny and white. The andrecium consists of 3 stamens connate by connective. The gynecium consists of a 1-celled ovary, a very short and thick style, and a subsessile and a truncate stigma. The ovule

Uses: In Malaysia, the dried roots are applied externally or used internally to treat fever. In Indonesia, a paste made from the powdered leaves is applied externally to soothe contusion and bone fracture, and a decoction of the leaves is drunk to stop vomiting. Another species, Chloranthus spicatus (Thunb.) Nak. (Chloranthus inconspicuus SW.), is a Chinese remedy used to treat malaria, relieve coughs, heal boils and carbuncles, treat fever and to invigorate health. It will be interesting to know whether further study on this plant will disclose any molecules with anti-inflammatory and/or antibacterial properties.

Subclass Magnoliidae

39

Fig. 23. Chloranthus eliator R. Br. ex Link.

is solitary and orthotropous. The fruits are succulent, 1.2 cm long, pulpy and white berries (Fig. 23). Warning: Caution must be taken as the toxic effects of this plant are unknown. Sarcandra glabra (Thunb.) Nak. [From Greek, sarkos = flesh, andros = man and from Latin, glaber = free from hairs] Physical description: It is an understorey herb which grows to a height of 1.2 m. It is native to the mountain forests of India, China and Malaysia. The stems are cylindrical, glabrous, dark green and articulate. Leaves: simple, glabrous, glossy, serrate, opposite and very thin. The blade is elliptic lanceolate, with an acute apex and an acuminate base, measuring 12.5 cm–18 cm×5 cm.The petiole is 6 mm–1.3 cm long, connate and forms a short stipular sheath. The flowers are small, in terminal, 1.5 cm long, and lax spikes. The

Synonymy: Chloranthus glaber (Thunb.) Nak.; Chloranthus brachystachys Bl., Chloranthus monander R.Br., Sarcandra chloranthoides Gardn. Common names: Sarcandra, glabrous Sarcandra; karas turan (Indonesian). Uses: In China, Sarcandra glabra (Thunb.) Nak. is applied externally to soothe bone fracture and contusion and a decoction of the leaves is used to stop vomiting. In India, this plant is used to invigorate health. In Indonesia, a mixture of stems, roots and leaves is used to treat fever, venereal diseases, stop spasms and to invigorate health. In Malaysia, the leaves are used to scent tea or to add bulk. In the Philippines, an infusion of the plant is drunk to assuage headache. In Vietnam, a tea-like beverage of the plant is used to relieve cough.

40

Division MAGNOLIOPHYTA

flowers are sessile, in connate pairs of male and female with small bracts. The male flower shows a short stamen, the anther of which is 4-celled. The ovary is 1-celled and contains a single ovule.The style is short and the stigma is subsessile and truncate.The fruits are bright red, succulent, glossy, globose, apiculate, and 5 mm diameter berries (Fig. 24). Pharmaceutical interest: Analysis of Sarcandra glabra (Thunb.) Nak. and its medicinal preparations by capillary electrophoresis has been reported by Fig. 24. Sarcandra glabra (Thunb.) Nak. Zheng et al., 2003. The plant is interesting because it accumulates betulinic acid which might hold potential for the treatment of melanoma, Human Immunodeficiency Virus and bacterial infection. Twenty-six cases of idiopathic thrombocytopenic purpura were clinically treated with Sarcandra glabra (Zhang JZ, 1981). COOH Are pentacyclic triterpenes involved in the medicinal uses mentioned above? HO

Reference

Betulinic acid

Zhang JZ. (1981) J Tradit Chin Med 1(1): 61–62.

Warning: Caution must be taken as the toxic effects of this plant are unknown.

2. Family PIPERACEAE C. A. Agardh 1825 nom conserv., the Pepper Family Physical description: The family Piperaceae comprises of 10 genera and about 2000 species of tropical herbs, climbers and treelets known to elaborate isoquinoline and piperidine alkaloids as well as styryl-lactones. Like Chloranthaceae, the stems are articulate. The leaves are simple, alternate and stipulate. The blade is often cordate. The flowers are tiny, without perianth, and packed in dense and succulent spikes. The andrecium comprises of 1–10 stamens, and the gynecium consists of a superior and 1-celled ovary containing a single orthotropous ovule. The fruits are capsular or drupaceous.

Subclass Magnoliidae

41

Pharmaceutical interest: Black Pepper O (British Pharmaceutical Codex, 1949) conO N sists of the dried unripe fruits of Piper nigrum L. which have been used since time O immemorial in India. This spice at doses ranging from 300 mg to 600 mg stimulates Piperine the taste-buds, produces a reflex increase in gastric secretion, treats fever and promotes urination. White pepper consists of dried unripe fruits of Piper nigrum L. deprived of the outer part of the pericarp. The taste of peppers is due to piperine, a piperdine alkaloid. Other Piperaceae are Piper longum (Long Pepper, Indian Pharmaceutical Codex, 1955), Piper methysticum Forst. (Kava, British Pharmaceutical Codex, 1934) and Piper betle (British Pharmacopoeia, 1934). A beverage prepared from the roots of Piper methysticum Forst. or kava has been used for centuries by a number of Polynesian ethnic groups to calm and to promote sleep, and although toxic, it has been marketed in Europe to treat sleeping disorders and anxiety. The leaves of Piper betle are mixed with lime and the scraping of Areca nuts for social purposes in Asia. About 30 species of plants classified within the family Piperaceae are of medicinal value in the Asia-Pacific. A growing body of evidences indicates that lignans of Piperaceae might hold potential for the treatment of cancers. Piper cubeba L. f [From Greek, peperi = pepper and from Arabic, kababah = cubeb] Physical description: It is a climbCommon names: Java pepper, ing shrub which grows to a length of cubebs, or tailed pepper; lada berekur 1 m in tropical Asia. The plant is native (Malay); tieu that (Vietnamese); thippli to Indonesia and Malaysia. The stems (Tamil); poivre de Java (French). are glabrous, articulate and succulent. Leaves: simple and alternate. The petiole is 1.5 cm–1.7 cm long, velvety, and channeled. The blade is broadly elliptic, velvety underneath, very thin, and 11 cm × 6.4 cm–8.5 cm × 4.8 cm. The margin is wavy, the apex of the blade is acuminate, and the base is asymmetrical and cordate. The blade shows 5–7 pairs of secondary nerves which are raised on both surfaces. The inflorescences are 4 cm × 3 mm spikes (Fig. 25). History: The dried unripe fruit forms the condiment cubebs. Cubebs (British Pharmaceutical Codex, 1934) consists of the dried unripe fully-grown fruit of Piper cubeba L. f. It was formerly employed as a urinary antiseptic (liquid extract; 1 in 1; dose 2 mL–4 mL). Lozenges of cubebs have been used to treat bronchitis. Cubeb

O O

O O O (-) Cubebin

OH

42

Division MAGNOLIOPHYTA

Oil (British Pharmaceutical Codex, 1949) is the oil obtained by the distillation of cubebs. It has been used as an emulsion or in capsules as a urinary antiseptic at doses of 0.3 mL to 1.2 mL, and to make cosmetics. A British Standard Specification for cubeb oil (B.S. 2999/5: 1965) has been published by the British Standards Institution.

Fig. 25. Piper cubeba L. f. From: KLU Herbarium 33497. Flora of Malaya. Date: 1979. Geographical localization: Nursery Garden, Dept of Botany, U.M. Obtained from AGR. RES. Center Semongok, Kuching, Sarawak, Malaysia. Field collector & botanical identification: KG Peare.

Uses: The fruits of Piper cubeba L. have been used in Europe as a spice as early as the 11th century. It has the repute of being antiseptic. In China, the fruits of Piper cubeba L. are eaten to promote digestion, and to stop vomiting. In Indonesia, Piper cubeba L. is used to treat venereal diseases and dysentery. In Taiwan, Piper cubeba L. is used to treat diabetes, gonorrhea, and to promote appetite. In Malaysia, Piper cubeba L. is used during confinement.

Pharmaceutical interest: The fruit of Piper cubeba L. contains terpenes, sesquiterpenes and some lignans including the dibenzylbutyrolactone lignan (−)-cubebin. The anti-viral, antifungal, antibacterial and cytotoxic potential of (−)-cubebin awaits further experimentation. Note that cubebin, isolated from the crude hexane extract of the leaves of Zanthoxyllum naranjillo (Family Rutaceae), protects rats against edema induced by carrageenan and prostaglandin PGE2 and protects mice against the pain caused by both acetic acid and PGI2 in mice (Bastos JK et al., 2001). In addition (−)-cubebin derivatives abrogate the survival of amastigote forms of Trypanosoma cruzi (de Souza VA et al., 2005). References Bastos JK, et al. J Ethnopharmacol 75: 279–282. De Souza VA, et al. (2005) Bioorganic & Medicinal Chemistry Letters 15 (2): 17: 303–307.

Subclass Magnoliidae

43

Peperomia pellucida (L.) HBK. [From Greek, peperi = pepper and homoios = resembling and from Latin, pellucidus = transparent] Common names: Shiny bush; pansit pansitan (Filipino). Uses: In Indonesia, Peperomia pellucida (L.) HBK. is used to assuage headaches and to treat colic. In the Philippines, Peperomia pellucida (L.) HBK. is used to heal abscesses and boils.

Physical description: It is a dwarfy herb which grows to a height of 20 cm. Fig. 26. Peperomia pellucida (L.) HBK. The plant is native to South America. It is very common and can be seen almost everywhere, particularly in pots besides ornamental plants. The stems are fleshy and translucent. Leaves: simple, alternate and without stipules. The petiole is 5 mm–7 mm long The blade is cordate, very thin, translucent, glaucous underneath and 1.7 cm × 2 cm–9 mm × 1.1 cm. The inflorescences are 4.5 cm–5 cm long and succulent spikes facing the leaves (Fig. 26). Pharmaceutical interest: A methanol extract of Peperomia pellucida (L.) HBK. assuages the pain of mice experimentally injured with acetic acid (Adeyemi O et al., 2001).The antiseptic and analgesic properties of the plant have been confirmed (Khan MR et al., 2002; Arrigoni-Blank MF et al., 2004). Is (+)epi-α-Bisabolol or lignans involved here? (Villegas LF et al., 2002).

H OH

H

Bisabolol

References Adeyemi O, et al. (2001) J Nat Prod 65(2): 248–250. Arrigoni-Blank MF, et al. (2004) J Ethnopharmacol 91(2–3): 215–218. Khan MR, et al. (2002) Fitoterapia 73(3): 251–254. Villegas LF, et al. (2002) Fitoter 72(1): 57–58.

Warning: Caution must be taken as the toxic effects of this plant are unknown.

44

Division MAGNOLIOPHYTA

D. Order ARISTOLOCHIALES Lindley 1833 This order consists of the single family Aristolochiaceae.

1. Family ARISTOLOCHIACEAE A. L. de Jussieu 1789 nom. conserv., the Birthwort Family Physical description: The family Aristolochiaceae consists of about 5 genera and 300 species of foetid climbers and herbs thought to have originated directly from the order Magnoliales from which is inherited the ability to produce toxic isoquinolines and their derivatives nitrophenanthrene alkaloids, and essential oils (Appendix I). Aristolochiaceae are usually bitter. The stems of woody species are articulate and show broad Menispermaceae-like medullary rays in cross-section. The leaves are simple, without stipules, often with oil-secreting cells, alternate, entire or lobed. Aristolochiaceae can be easily spotted in the field because of their flowers which are 3-lobed or pipe-shaped.The andrecium consists of 6 or more stamens in 1 or 2 whorls around the apex of the ovary or stylar column. The ovary is 4–6-celled and the style is columnar. The fruits are capsular or baccate. Pharmaceutical interest: Classical examples of Aristolochiaceae are Aristolochia reticulata (serpentary, red river snakeroot, and Texan snakeroot) and Aristolochia serpentaria (Virginian snakeroot), both of which are used to treat dyspepsia, considering their bitterness. Other examples are Aristolochia clematis (birthwort) and Asarum europeaum which were used in European medicine. The dried rhizomes, roots and leaves of Asarum europeaum (asarabaca) are used to induce vomiting, relieve the bowels of costiveness, and assuage headache, and are listed in the Spanish Pharmacopoeia 1954.The sodium salt of aristolochic acid has been given per os to treat a number of inflammatory conditions, but it is nephrotoxic in humans and in animals, as well as carcinogenic in rodent. About 20 species of plants classified within the family Aristolochiaceae are used for medicinal purposes in the Asia–Pacific. These are often used to counteract snakepoisoning, promote urination and menses, assuage stomachaches and to treat dropsy and skin diseases. The therapeutic potential of most Aristolochiaceae is unknown but one might set the hypothesis that the rhizomes of Aristolochia species counteract snake-poison and inhibit inflammation on account of a probable inhibition of phospholipase A2 by isoquinoline alkaloids through a steroidal-like mechanism. Of interest are also the antimicrobial and cytotoxic potential of Aristolochiaceae alkaloids.

Subclass Magnoliidae

45

Apama corymbosa (Griff.) Willd. [From Greek, korumbos = cluster] Physical description: It is a shrub which grows to a height of 3 m. The plant is a common sight along the jungle tracks of Malaysia and Sumatra. The stems are glaucous, soft, zig-zagshaped and articulate. Leaves: simple, 15 cm × 6 cm, glabrous, alternate and without stipules. The blade is lanceolate and pubescent and shows 3–5 pairs of secondary nerves. The petiole is 5 mm long. The inflorescences are terminal, pubescent, panicles of small yellowish-green flowers. The perianth comprises of 3 yellowish-green lobes around a black mouth. The andrecium Fig. 27. Apama corymbosa (Griff.) Willd. consists of 1 whorl of 8–10 stamens. The stigma is disc-shaped. The fruits are capsular, 25 cm–30 cm × 4 mm, 4 keeled and contain several triangular seeds (Fig. 27). Pharmaceutical interest: The general tendency in terms of medicinal uses suggests the anti-inflammatory potential of the plant. It would not be surprising as antibacterial alkaloids occur in Bragantia wallichii (Panse MV et al., 1971). The same group of alkaloids is very likely to be present here and it would be interesting to assess their activity towards the enzymatic activity of phospholipase A2 , or cyclo-oxygenase, key enzymes of inflammation.

Synonymy: Bragantia corymbosa Griff. Common names: Akar julong, bukit, akar surai (Malay). Uses: In Java, the stems and leaves are applied externally to counteract snake-poison. In Malaysia, the pounded leaves are applied to the gums or laid onto the hollow of teeth to assuage toothache. The roots are mixed with the kernel of Myristica fragrans Houtt. to make a protective postpartum medicine.

Reference Panse MV, et al. (1971) Indian J Med Res 59(8): 1190–1193.

Warning: Caution must be taken as the toxic effects of this plant are unknown.

46

Division MAGNOLIOPHYTA

Apama tomentosa (Bl.) O. Ktze. [From Latin, tomentum = padding of wool] Common name: Creeping apama.

Uses: In Indonesia, the juice expressed from the leaves and stems is drunk to relieve cough. The plant is used as an ingredient in a remedy to promote urination. Apama tomentosa (Bl.) O. Ktze. is used to counteract snake-poison. Malays use this plant to heal boils and to counteract putrefaction. The pharmacological potential of this herb is unknown.

Fig. 28. Apama tomentosa (Bl.) O. Ktze.

Physical description: It is an understorey herb which grows to a height of 80 cm. It is found in Malaysia, India and Indonesia. The stems are woody and tomentose. Leaves: 12 cm–22 cm × 9 cm–14 cm, simple, and without stipules. The petiole is tomentose and 2 cm long. The blade is leathery, obovate, tomentose underneath, and glabrous above except for the nerves. The apex of the blade is acute and the base cordate. The tertiary nerves are scalariform, sunken above and filled with hairs. The margin is slightly recurved. The inflorescences are 9 cm long and tomentose racemes from the base of the stems. The flowers are tiny, dull red, and comprise of 6 stamens. The fruits are capsular (Fig. 28). Warning: Caution must be taken as the toxic effects of this plant are unknown. Aristolochia indica L. [From Greek, aristo = best and lochia = delivery and from Latin, indica = from India] Physical description: It is a climber Common names: Indian aristolochia native to India. Leaves: foetid, simor Indian birthwort; ishvara (Sanskrit), ple, and 4 cm–12 cm × 1.5 cm–7 cm. adagam (Tamil). The blade is broad or linear-oblong to obovate-oblong, subtruncate or subcordate, glabrous and the margin is undulating. The apex is obtusely acuminate and the base cuneate. The inflorescences are few flowered axillary racemes. The flowers are greenish-white with

Subclass Magnoliidae

47

a 5 cm long pipe-shaped perianth. The andrecium comprises of 6 anthers. The gynecium consists of 6 carpels united to form a compound ovary. The fruits are 6-valved, 3.5 cm–5 cm long, oblong or globose capsules. The seeds are deltoid-ovate, acute, flat and winged (Fig. 29). Pharmaceutical interest: The rhizome of Aristolochia indica L. contains aristolochic acid together with other phenanthrene derivatives, Nglycosides and steroids. Glucocorticoidal properties:The antiinflammatory property of Aristolochia species is probably on account of a direct interaction of aristolochic acid and derivatives with the enzymes of the inflammatory process. For Fig. 29. Aristolochia indica L. example, aristolochic acid inhibits in vitro and dose-dependent phosUses: In India, the rhizome of Aristolochia pholipid hydrolysis by the human indica L. is used to treat impotence, synovial fluid phospholipase A2 , resolve inflammation, induce vomiting, treat malarial fever and to invigorate snake venom phospholipase A2 , health. In Burma, the leaves are applied porcine pancreatic phospholipase externally to treat skin diseases. In the A2 and human platelet phosphoPhilippines, the rhizome is used to counlipase A2 (Vishwanath BS et al., teract insect-poison, combat fever, reg1988). An ethanolic extract of rhiulate menses, to invigorate the body, zomes of Aristolochia indica L. and to assuage intestinal discomfort. In given postcoitally decreases the ferVietnam, the rhizome is used to treat tility of rats and hamsters (Che CT malaria, dropsy and fever, and to stimulate et al., 1984). The concomitance of appetite. A tincture of dried stems and rhiboth anti-inflammatory and postzomes of Aristolochia indica L was used in coital abortive properties brings to Britain to promote digestion (British Pharmaceutical Codex, 1934). mind the property RU486 or mifepristone, a synthetic steroid antagonist of both progesterone and glucocorticoid receptors, which is used (tablets 50 mg or 200 mg) to stop pregnancy (Fig. 30). Aristolic acid characterized from Aristolochia indica L. is another phenanthrene derivative which has a structure similar to progesterone. This natural product

48

Division MAGNOLIOPHYTA CH3 H3C

N

CH3

HO

O RU486 O O

O

COOH NO2 OCH3

O Progesterone

Aristolochic acid

Fig. 30. Note the similitude of chemical structure of RU486, aristolochic acid, and progesterone.

inhibits nidation in mice when given from the first day of pregnancy. Histological observations revealed an impairment of development (decidualization), and a decrease of the uterine weight. Aristolic acid may interfere with the steroidal conditioning of the uterus making it therefore hostile to the ovum implantation (Ganguly T et al., 1986). A methyl ester of aristolic acid is strongly abortifacient per os (100% at 60 mg/Kg; Pakrashi A et al., 1978) as well as p-coumaric acid (single dose of 50 mg/Kg; Pakrashi A et al., 1979) and a sesquiterpene (Pakrashi A et al., 1977). H3CO

O

COOH N

HO O

NO2

CH3

H3CO OCH3 Aristolochic acid

OH Isoboldine

Other pharmacological properties: Both ethanol and alkaloidal extracts of Aristolochia papillaris inhibit the contraction caused by oxytocin on non-pregnant rat uterus preparation. Moupinamide, coclaurine and isoboldine, 3 isoquinoline alkaloids characterized from an alkaloidal fraction of Aristolochia papillaris relax the smooth muscle of guinea-pig preparation. Propranolol inhibits the effect of coclaurine and isoboldine, suggesting a muscle relaxant property via adrenoreceptors (Lemos VS et al., 1993). An acetylated N-glycoside characterized from Aristolochia contorta inhibits significantly the proliferation of Gram-positive bacteria in vitro. (Lee HS et al., 1992.) References Che TC, et al. (1984) J Nat Prod 47(2): 331–341. Ganguly T, et al. (1986) Contraception 34(6): 625–637. Lee HS, et al. (1992) J Nat Prod 55(9): 1165–1169.

Subclass Magnoliidae

49

Lemos VS, et al. (1993) J Ethnopharmacol 40(2): 141–145. Pezzuto JM, et al. (1988) Mutat Res 206(4): 447–454. Pakrashi A, et al. (1977) Ind J Exp Biol 15(12): 1197–1198. Pakrashi A, et al. (1979) Contraception 20(1): 49–54. Vishwanath BS, et al. (1988) Inflammation 12(6): 549–561.

Warning: Exposure to Aristolochia species is associated with the development of renal interstitial fibrosis and urothelial cancer in humans. Health professionals should be aware that in traditional Chinese medicine, Aristolochia species are considered interchangeable with certain other herbal ingredients and are also sometimes mistaken for Stephania tetrandra, Akebia, Asarum, Clematis species and Cocculus species in herbal remedies. Aristolochic acid is a typical example of natural product (P388 ED50 = 0.58 µM) which is both cytotoxic and mutagen (Salmonella thyphimurium TA100, TA102, TA1537, TA677 strains; Pezzuto JM et al., 1988). Aristolochia tagala Cham. [From Greek, aristo = best and lochia = delivery Physical description: It is a climber which grows in the geographical zone

Fig. 31. Aristolochia tagala Cham. From: Ex. Herbario BC Stone. Field collector & botanical identification: BC Stone, 4 Jul 1977. Geographical localization: altitude 1000 ft, Selangor, Kuala Lumpur, University of Malaya campus, Malaysia.

Synonymy: Aristolochia roxburghiana Klotzsch. Common names: Roxburgh’s Aristolochia; kalayar, puyan, kunit (Indonesian); akar ketola hutan (Malay); goan-goan, nagerus, timbangan (Filipino); krachao mot, krachao pheemot (Thai); daaly khoos (Vietnamese).

spanning India to Papua New Guinea. The stems are smooth, terete and glabrous. Leaves: light green, spiral and without stipules. The petiole is 2.5 cm–3.5 cm long. The blade is sagitate, 14 cm × 7.5 cm–12 cm × 7 cm, and leathery. The margin is recurved. The blade shows 3–5 pairs of secondary nerves.The tertiary nerves are showily scalariform underneath. The fruits are axillary, 5-lobed, basket-shaped, and 2 cm × 1.5 cm–3 cm × 2.5 cm when opened. The seeds are numerous, flat and small (Fig. 31).

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Division MAGNOLIOPHYTA

Pharmaceutical interest: The usefulness of Aristolochia tagala Cham. in dermatology has been assessed (Konigsbauer H, 1968). It will be interesting to learn whether more intensive future research on Aristolochia tagala Cham. will disclose any molecules of therapeutic interest.

Uses: In Indonesia, the leaves are used to resolve swollen limbs and to treat bilious disorders. In Malaysia, the pounded leaves are used to treat fever. In the Philippines, a powder of the roots is used to invigorate health, to treat infantile tympanites and to promote digestion and menses.

Reference Konigsbauer H. (1968) Z Haut Geschlechtskr 43(4): 153–159.

Warning: Caution must be taken with this plants as its toxic effects are unknown. Asarum sieboldii Miq. [From Greek, asarum = a plant, described by Dioscorides and Pliny, and after Philip Franz Von Siebold (1796–1866), a German naturalist who explored Japan] Physical description: It is a rhizomatous herb found on the shady stream banks and in the deciduous

Synonymy: Asarum heterotropoides Fr. Schmidt var. mandshuricum (Maxim.) Kitawaga. Common names: Chinese wild ginger; xi xin (Chinese).

Fig. 32. Asarum sieboldii Miq. From: Herbarium 10071. Ex. Herbario Universitatis Imperialis Tokyoensis. Field collector & botanical identification: H Nakai & K Obuko, 23 May 1965. Geographical localization: Japan: Nagano Pref. Shiya-Kosen Uchiyama-Mura, Minamisaku — Gun, altitude 900 m–1,000 m.

forests of China and Japan. The plant grows to a height of 20 cm– 30 cm. Leaves: simple, spiral and without stipules. The petiole is 9 cm–13.5 cm × 2 mm–3 mm. The blade is cordate, irregular, very thin and 5.5 cm × 5 cm–10 cm × 11 cm. The blade shows a few secondary nerves which originate from the base. The flowers are solitary, axillary and dark purple. The flower pedicel is 5 mm–2 cm long. The perianth is bellshaped, 3-lobed and 1.5 cm × 1.4 cm (Fig. 32).

Subclass Magnoliidae

51

Pharmaceutical interest: The roots Uses: In Japan and China, the entire contain 3% of essential oil which complant is used to treat colds and an prises of methyleugenol, phenol, safinflamed mouth, to curb vomiting, and role, pinene, asarinin, eucarvone, and to assuage headache and toothache. palmitic acid (Nagasawa, 1961). The The roots are used to induce vomiting, cough, perspiration, urination, and anti-inflammatory property of Asarum to purge the bowels. The roots are sieboldii is confirmed (Qu SY et al., also used to treat epilepsy, rheumatic 1982). Phenylpropanoids such as affections, nasal polyps and ulcers in methyleugenol could mediate both the mouth. In Korea, the roots and the expectorating and analgesic propstems are used to treat colds and to erties as demonstrated in Asarum kill insects. europaeum L. (Gracza L., 1981; Belova LF et al., 1985). The effect of Asarum sieboldii on the left ventricular function of dogs is known (Chen ZZ et al., 1981). The plant is interesting because its analgesic property involves bradykinin, histamine and opioid receptor-mediated pathways (Kim SJ et al., 2003). References Belova LF, et al. (1985) Farmakologiia i Toksokologiia 48(6): 17–20. Chen ZZ, et al. (1981) Yao Hsueh Hsueh Pao 16(10): 721–727. Gracza L. (1981) Planta Med 42(2): 155–159. Kim SJ, et al. (2003) J of Ethnopharmacol 88(1): 5–9. Nagasawa M. (1961) J Pharm Soc Japan 81: 129–138.

Warning: Caution must be taken as the toxic effects of this plant are unknown. Thottea dependens Klotzsch [From Latin, pendere = be suspended] Physical description: It is an uncomUses: The plant is probably mon shrub found in the open forests counter-irritant. In Malaysia, a paste and old rubber estates of Malaysia. made from the leaves is applied The stems are smooth and velvety. externally to treat skin diseases and Leaves: alternate, simple and without fever, and to stimulate the skin to stipules. The petiole is stout, velvety redness. It will be interesting to know and 5 mm long. The blade is oblongif further study on this plant discloses any molecules of therapeutic interest. ovate, leathery, glabrous on the surface and velvety underneath. The apex is acute-acuminate and the base acute-round. The margin is entire and recurved. The midrib is sunken above and strongly raised below. The blade shows 9 to 12 pairs of secondary nerves which are flat above and raised below, and scalariform tertiary nerves. The inflorescences are velvety and axillary

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Division MAGNOLIOPHYTA

racemes. The flowers are bell-shaped, 3-lobed, and 10.5 cm × 7 cm–7 cm × 8 cm. The perianth is dark purple and showily nerved. The pedicel is velvety and 1.4 cm–9 cm. The fruits are 14 cm–7 mm–16.5 cm × 5 mm, velvety and obscurely quadrangular capsules. The seeds are tiny and numerous (Fig. 33). Warning: Caution must be taken as the toxic effects of this plant are unknown.

E. Order RANUNCULALES Lindley 1833

Fig. 33. Thottea dependens Klotzsch. From: Herbarium 6437. Field collector & botanical identification: MED Poore. Flora of Malaya, 12 Oct 1964. Geographical localization: Fort Iskandar, shady locality in Belukar. From Herbarium 037272. Field collector & botanical identification: SC Chin & Mustafa. 14 Feb 1985. Geographical localization: Kampung Sungai Layang, Rembau, Negeri Sembilan, Malaysia.

The order Ranunculales consists of 8 families and about 3200 species of herbs, known to abound with triterpenoid saponins, sesqui-, di- and triterpenes, diterpene alkaloids, lignans and isoquinolines inherited from the Magnoliales (Appendix I). Ranunculales is a common ancestor to both the Caryophyllales and Papaverales to which it brings triterpenoid saponins and isoquinoline alkaloids respectively (Appendix I). More than half of the species belong to the family Ranunculaceae, and most of the others belong to the family Berberidaceae and the family Menispermaceae.

1. Family RANUNCULACEAE A.L. de Jussieu 1789 nom. conserv., the Buttercup Family Physical description: The family Ranunculaceae, a vast O O group which consists of 50 genera and 2000 species of rhizomatous herbs, is widespread in temperate and boreal regions. The leaves are simple, without stipules, radical and alternate and variously compound or dissected. The flowers Protoanemonin are bisexual, actinomorphic, and solitary to paniculate. The calyx comprises of 3–8 sepals which are imbricate or valvate, deciduous and sometimes petaloid. The corolla comprises many to few and free petals, mainly with a nectariferous claw, showy, yellow, white, blue or pink. The stamens are numerous, spirally

Subclass Magnoliidae

53

arranged and centripetal, free, distinct, with long and thin filaments and welldefined anthers. The gynecium consists of many free carpels, each with a style. The ovules are anatropous, numerous or solitary. The placentation is marginal or basal. The fruits are follicles, achenes or berries. Classical examples of Ranunculaceae are Ranunculus acris (buttercup) and the ornamental Aquilegia vulgaris and Helleborus orientalis. Pharmaceutical interest: In ancient times, OH OCH 3 decoctions of Ranunculus were used to OCH3 make arrow poison, punish criminals, and O put to death, the elderly with incurable and painful diseases, and Dioskurides (1st OH O N century A.D.) noted: “Ranunculus. . . of this OCOCH3 there are many kinds, but ye faculty is one, HO OCH3 sharp and too much exulcerating”. A large H3CO number of Ranunculaceae are irritants on account of a glycoside called ranunculin, Aconitine which readily breaks down in bruised plant tissue by enzyme action to release protoanemonin, which is a volatile, strongly irritant and unstable terpenoid lactone. Other toxic principles of Ranunculaceae are diterpene alkaloids, isoquinoline alkaloids, and cardiac glycosides. Diterpene alkaloids: Examples of diterpene alkaO loids are aconitine, elatine and delphinine. The N CH dried roots of Aconitum napellus L. (wolfsbane root) O 3 O O H containing not less than 0.5% of alkaloids calculated as aconitine (Aconite, British Pharmaceutical H Codex, 1963) was formerly used as tincture in the OCH3 early stages of fever and as liniment in the treatment of neuralgia, sciatica and rheumatism, but OCH3 it has been dropped because it is too toxic. Oral Hydrastine intake of aconitine is followed shortly by tingling of the tongue, mouth, stomach and skin as well as numbness, anesthesia, nausea, vomiting, diarrhea, excessive salivation, incoordination, muscular weakness, vertigo and death from paralysis of the heart or the respiratory center. Elatine, a diterpene alkaloid obtained from Delphinium elatum, has been used to relax muscles similar to tubocurarine at a dose of 10 mg, 3 to 5 times daily. Staphisagria (British Pharmaceutical Codex, 1949) consists of the dried ripe seeds of Delphinium staphisagria L. (stavesacre seeds) containing 1% of alkaloids, of which delphinine. It has been used to combat lice infestation. Isoquinolines: Classical examples of isoquinolines of Ranunculaceae are hydrastine (a phthalyltetrahydroisoquinoline) and berberine (a protoberberine).

54

Division MAGNOLIOPHYTA

Hydrastis (British pharmaceutical Codex, 1949) consists of the dried rhizome and roots of Hydrastis canadensis L. (golden seal) containing not less than 1.5% of hydrastine. It has been used to stop excessive uterine hemorrhage and as a bitter stomachic. Hydrastine hydrochloride (British pharmaceutical Codex, 1949) constricts peripheral vessels and causes uterine contraction and arrests uterine hemorrhage. It has been used at a dose of 15 mg–60 mg but it is of doubtful value. Hydrastis canadensis L. contains berberine which is antibacterial, fungicidal and antiprotozoal, and it decreases intestinal peristalsis. Cardiac glycosides: Hellebore (British Pharmaceutical Codex, 1934) consists of the dried rhizomes and roots of Helleborus niger (Christmas rose) which contains cardiac glycosides of the bufadienolide type including helleborin, helleborein and hellebrin. Hellebrin has a strophantin-like action and has been used as a cardiotonic. The aerial parts of Adonis vernalis L. (Adonis, French Pharmacopoeia 1965) have been used instead of digitalis as a tincture (1 in 10, dose 10 to 30 minims). It contains a number of cardenolides among which cymarin is the chief active constituent. About 50 species of Ranunculaceae including Ranunculus sceleratus L. and Coptis japonica (Thunb.) Mak are of medicinal value in Asia. These are commonly used to assuage pain, to counteract putrefaction, and to treat fever and dysentery. Coptis japonica (Thunb.) Mak. [From Latin, japonica = from Japan] Physical description: It is a herb which grows to a height of 30 cm. It is found in China and Japan. Leaves: originate from a rhizome. The petiole is 12 cm– 20 cm long and channeled. The petiolules are channeled and 1 cm–2.5 cm long.The blade consists of 3 folioles which are deeply incised, very thin and 6.7 cm × 5.5 cm–4.7 cm × 3.5 cm. The midrib is sunken above and raised below. The folioles show 4 to 5 pairs of secondary nerves. The flowers are small and white, and attached to reddish pedicels arising from the rhizomes. The fruits consist of 7–9, papery and 1.1 cm–1.3 cm × 4 cm pediceled carpels hooked at the apex (Fig. 34).

Synonymy: Coptis anemonaefolia Sieb. & Zucc. Common names: Japanese goldthread; huang lia (Chinese). Uses: In Japan, the rhizome of Coptis japonica (Thunb.) Mak. is used to promote appetite and digestion. In Cambodia, Laos and Vietnam, Coptis japonica (Thunb.) Mak. is used to assuage headaches, soothe itchiness and treat eczema marginatum. In Malaysia, Coptis japonica (Thunb.) Mak. is used to resolve eye inflammation.

Subclass Magnoliidae

55

Pharmaceutical interest: The rhizome of Coptis japonica (Thunb.) Mak. is known to accumulate several sorts of protoberberines, among which are palmatine, jatrorrhizine and berberine, the last being a powerful antibacterial agent. Recent research shows that berberine chloride from the rhizome of Coptis japonica (Thunb.) Mak. inhibits aldose reductase isolated from male Sprague-Dawley rats (Lee HS 2002). Berberine and palmatine from Coptis japonica (Thunb.) Mak. inhibit catecholamine by impeding the activity of tyrosine hydroxylase in PC12 cells with IC50 values of 9.5 µg/mL and 7.7 µg/mL respectively Fig. 34. Coptis japonica (Thunb.) Mak. (Lee MK et al., 1996). Jatrorrhizine and From: KLU Herbarium 17902. Ex. Herb. berberine extracted from the rhizome Universitatis Tokyoensis. Geographical localof Coptis chinensis are monoamine ization: Japan, Niigita Pref., Iwahune-gun, oxidase inhibitors which might hold Sekikawa-mura, near Takanosu-onsen, 27 Apr 1972, altitude: 400 m, Japan. Field collector & some potential for the treatment of botanical identification: M Togashi & Y Tateishu. depression. Jatrorrhizine inhibits noncompetitively both MAO-A and -B from rat HO brain mitochondria with the IC50 value of 4 N+ and 62 µM, respectively, berberine competi- H CO 3 tively inhibits MAO-A with an IC50 value of OCH3 126 µM (Kong LD et al., 2001). Several lignans, including pinoresinol and isolariciresinol, OCH3 isolated from Coptis japonica (Thunb.) Mak. inhibit the production of TNF-α, (Cho JY et al., Jatrorrhizine 2000; 2001). References Cho JY, et al. (2000) J Nat Prod 63(9): 312–316. Cho JY, et al. (2001) Planta Med 67(4): 312–316. Kong LD, et al. (2001) Planta Med 67(1): 74–76. Lee MK, et al. (1996) Planta Med 62(1): 31–34. Lee HS. (2002) J Agric Food Chem 50(24): 7013–7016.

Warning: Caution must be taken as the toxic effects of this plant are unknown.

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Division MAGNOLIOPHYTA

Ranunculus sceleratus L. [From Latin, rana = frog and from Greek, selinon = parsley] Physical description: It is a herb which Common names: Celery-leaved grows to a height of 60 cm. It is found in buttercup, cursed crowfoot; the ditches and paddles of the temperate grenouillette aquatique, mort aux regions. The stems are succulent, inflated vaches (French); shih lung juei and glabrous. Leaves: radical, 1.8 cm– (Chinese); ranunculo mataboi 3.7 cm diameter, reniform and 3-fid. The (Portuguese); ranunculo malvado upper leaves are cauline, entire or 3-fid (Spanish); thach long noi (Vietnamese). and smaller. The petiole is slender, channeled, sheathing at the base and 1 cm– 4.5 cm long. The blade is very thin, deeply incised and shows nervations which are prominent on both surfaces. Inflorescences: axillary and solitary.The pedicels are 1 cm–3 cm long. The flowers are yellow, showy and 6 mm–1.2 cm in diameter. The sepals are oblong, pubescent and caducous. The corolla consists of 4–5 elliptic oblong petals. The fruits are numerous hooked and free 3 mm × 5 mm follicles (Fig. 35). Uses: Ranunculus sceleratus L. has been used to raise blisters and as counter-irritant since time immemorial. In China, Ranunculus sceleratus L. is used to treat colds, arthritis and rheumatisms and to invigorate health. In Laos, Cambodia and Vietnam, the seeds are eaten to promote appetite and digestion, treat kidney diseases and heal abscesses.

Pharmaceutical interest: The plant contains tryptamine derivatives (Bhargava KP et al., 1965). A leaf extract of Ranunculus sceleratus L. displays a quick and broad fungicidal activity (Misra SB et al., 1978). An extract of Ranunculus sceleratus L. shows significant effects against epimastigote of Trypanozoma cruzi Bra C15C2 clone Fig. 35. Ranunculus sceleratus L. From: KLU in vitro with an IC50 value of 10.7 Herbarium 004451.Delhi University Herbarium. Geographical localization: Shakti Nagar, Delhi, µg/mL (Schinella GR et al., 2002). It India. 26 Feb 1961. Field collector & botanical will be interesting to know if further identification: Krishnan Kumar. Altitude: 620 ft, study on Ranunculus. sceleratus will rainfall 20”–50”.

Subclass Magnoliidae

57

disclose any molecules clinically active against Trypanozoma cruzi. In regard to the anti-rheumatic uses mentioned above, a pharmacological approach to the pro- and anti-inflammatory effects of the plant is reported by Prieto et al., 2003. References Bhargava KP, et al. (1965) Br J Pharmacol 25(3): 743–750. Mahran GH, et al. (1968) Planta Med 16(3): 323–328. Misra SB, et al. (1978) Experientia 34 (11): 1442–1443. Prieto et al. (2003) J Ethnopharmacol 89(1): 131–137. Schinella GR, et al. (2002) Fitoter 73(7–8): 569–575.

Warning: Ranunculus sceleratus L. is intensely irritating and produces violent blistering of the lips, tongue and skin on account of anemonin (Mahran GH et al., 1968). The plant can be mistaken for parsley and eaten resulting in fatal intoxication.

2. Family BERBERIDACEAE A. L. de Jussieu 1789 nom. conserv., the Barberry Family Physical description: The family Berberidaceae consists of about 13 genera and 650 species of woody herbs, shrubs and treelets which are widespread in the temperate regions of the Northern Hemisphere. The genus Berberis is by far the largest genus with some 500 species.The chemical weapons used here are mainly isoquinoline (berberine) alkaloids, occasionally quinolizidine alkaloids, and lignans and triterpenoid saponins. The stems are often woody and show typical broad medullary rays in transversal section.The leaves are simple or compound, alternate and without stipules. The flowers are hermaphrodite, hypogynous, and mostly trimerous. The sepals and petals are similar. The perianth consists of 2 series of sepals, and 4 series of petals. The andrecium consists of 6 stamens facing the petals, with short filaments, and with tetrasporangiate anthers which are dithecal and open by valves. The gynecium comprises of a single carpel which encloses a few anatropous ovules. The fruits are berries. The seeds are often arillate. Pharmaceutical interest: Berberis aristata is a herbal ingredient of Asian medicines used in UK to invigorate and to treat fever, and has been listed 3000 BC by the Caraka Samhits to treat obesity. The tubers of Leontice leontopetalum contain saponins and alkaloids and have been used for the treatment of epilepsy. Jeffersonia diphylla (twinleaf), Mahonia aquifolium, Hydrastis canadensis, Caulophyllum thalictroides and Podophyllum peltatum L. (May apple) have long been used by North American Indians for medicinal purposes.

58

Division MAGNOLIOPHYTA H3C

O O

O HO

OH

OH O

O

O O

O

O

O O

H3CO

O

OCH3

H3CO

OCH3

OCH3 OH

Podophyllotoxin

Etoposide

O O

N+ OCH3 OCH3 Berberine

The roots of Jeffersonia diphylla (twinleaf) and Mahonia aquifolium (Oregon grape) have been used to invigorate health. The dried rhizomes and roots of Hydrastis canadensis (Hydrastis, BHP) have been used to stop uterine hemorrhage. The rhizome of Podophyllum peltatum L. (May apple) has been used to remove warts and to relieve the bowels of costiveness. It contains podophyllotoxin, a cytotoxic lignan from which etoposide has been semisynthetically developed to treat lung cancer, lymphoma and leukemia. Berberidaceae abound with isoquinoline alkaloids of therapeutic value. One such compound is berberine (Chinese Pharmacopoeia, 1997) which is a broad spectrum antibiotic and antiprotozoal benzyltetrahydroisoquinolines alkaloid. Berberine is amphiphile and penetrates bacteria. It is bacteriostatic at low doses and bactericide at higher doses and is used to make antiseptic collyres in Europe. It destroys in vitro several sorts of bacteria, fungi and protozoa (Leishmania and Plasmodium). In the Asia-Pacific, a number of plants classified within the family Berberidaceae are used to invigorate health, treat fever and counteract putrefaction.

Subclass Magnoliidae

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Berberis thunbergii DC. [From Arabic, barbaris and after Common name: Japanese barberry. Carl Peter Thunberg (1743–1828), Swedish naturalist and favorite pupil of Linnaeus] Physical description: It is a spiny shrub of China and Japan which grows to a height of 1 m. The plant is often cultivated to decorate gardens and is even made into bonsais. Leaves: simple, without stipules, in groups, and sessile. The blade is spathulate, 1 cm–4 cm × 5 mm–1 cm, and reddish or green. The margin is slightly wavy and recurved. The secondary nerves are indistinct. The flowers are solitary, axillary and showy.The calyx comprises of 3 triangular sepals. The corolla comprises of 4 series of petals. The andrecium comprises of 6 stamens. The gynecium consists of a single-celled ovary. The fruits are ovoid, with red berries attached to the slender pedicels (Fig. 36). Uses: In China and Japan, the bark is used to cool, to expel intestinal worms, to counteract putrefaction and to check menorrhagia. A decoction of the stem and roots is used to wash the eyes. In Vietnam, a decoction of the plant is used to wash the eyes and to treat dental caries.

Fig. 36. Berberis thunbergii DC. From: KLU Herbarium 039313. Field Collectors: Benjamin C Stone, AE Schuyler & Emilie Russell. Geographical localization: United States of America, Pennsylvania, Hopewell Furnace/village National Historic Site “shunk cabbage”. Botanical Identification: Benjamin C Stone.

Pharmaceutical interest: It will be interesting to learn whether more intensive future research on Berberis thunbergii DC. will disclose any alkaloid of therapeutic interest. Note that Berberis thunbergii DC. contains berberine, oxyberberine, jatrorrhizine and other isoquinoline alkaloids which are probably responsible for uses mentioned above (Kawashima Y et al., 1969; Khamidov I et al., 1997).

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Division MAGNOLIOPHYTA

References Kawashima Y, et al. (1969a) Yakugaku Zasshi 89(10): 1386–1391. Khamidov I, et al. (1997) Khim Prir Soedin 5: 763–764.

Warning: Caution must be taken as the toxic effects of this plant are unknown. Caulophyllum robustum Maxim. [From Latin, caulis = stem; from Greek, phullon = leaf; and from Latin, robustus = robust] Physical description: It is a small woody shrub native to Japan.The plant is ornamental in temperate gardens. The stems are terete and glabrous. Leaves: consist of 2 pairs of folioles and a terminal one. Some folioles are pinnate, and the terminal one is 3lobed at the apex. The folioles are 5 cm–10 cm long, very thin, sessile, asymmetric and acute at the apex. Each foliole shows 2–3 pairs of secondary nerves. The margin of the blade is wavy or toothed at the apex. The inflorescences are axillary panicles of about 20 cm long. The fruits are blackish-blue berries of about 7 mm in diameter (Fig. 37). Uses: In China, the roots are soaked for 2 weeks in wine and the liquid is used externally to treat injuries caused by machines. The rhizome and roots of Caulophyllum thalictroides (Caulophyllum, British Pharmaceutical Codex, 1934) have been used to promote urination and menses, usually in the form of a liquid extract (1 in 1; dose of 0.6 mL to 2 mL).

Synonymy: Leontice robusa (Maxim.) Diels. Common name: Blue cohosh.

Fig. 37. Caulophyllum robustum Maxim. From: Herbarium KLU 040275. Field collector & botanical identification: Monica, 10 Aug 1988, altitude 600 m. Geographical localization: Ogawa Experimental Station. North Ibaraki, Japan.

Subclass Magnoliidae

61

COOH

HO

O OH OH O H OH O O OH

OH

OH Cauloside C

Pharmaceutical interest: Cauloside C, a pentacyclic glycoside isolated from Caulophyllum robustum Maxim., inhibits the synthesis of ergosterol in Saccharomyces carlsbergensis and inhibits the synthesis of RNA at the stage of 14 C uridine incorporation into the nucleotide pool of Saccharomyces carlsbergensis (Anisimov MM et al., 1972, 1977; 1977, 1978). Cauloside C interacts with cells pH-dependently and increases potassium leakage and calcium uptake. It might be a new biochemical tool for cell permeabilisation (Aminin DL et al., 1999). Note that cauloside C promotes the growth of fibroblasts cultured in vitro and hence has some healing properties. References Kennelly EJ, et al. (1999) J Nat Prod 62(10): 1385–1389. Aminin DL, et al. (1999) Comp Biochem Physiol A Mol Integr Physiol 1999 Jan; 122(1): 45–51. Anisimov MM, et al. (1972) Antibiotiki 17(9): 834–837. Anisimov MM, et al. (1977) Antibiotiki 22(9): 837–841. Anisimov MM, et al. (1978) Prikl Biokhim.Mikrobiol 14(4): 573–582.

H N

CH3

N H O N - Methylcytisine

Warning: N-methylcytisine from Caulophyllum thalictroides, acting as a teratogen in rat embryos cultured in vitro (Kennelly EJ et al., 1999).

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Division MAGNOLIOPHYTA

3. Family LARDIZABALACEAE Decaisne 1838 nom. conserv., the Lardizabala Family Physical description: The family Lardizabalaceae consists of 8 genera and about 30 species of twining woody climbers and shrubs which are strongly tanniferous and known to abound with triterpenoid saponins. The leaves are alternate digitately compound or rarely pinnate.The flowers are racemose, unisexual, actinomorphic and developing with the leaves from perulate buds. The calyx consists of 3 or 6 imbricate sepals. The corolla consists of 6 petals which are smaller than the sepals.The andrecium is made of 6 stamens which are free or connate. The gynecium consists of 3 carpels, each containing 1–numerous ovules. The fruits are succulent, colored and indehiscent ripe carpels. Pharmaceutical interest: A classical example of Lardizabalaceae is Akebia quinata (Thunb.) Decne. which is grown as a porch-vine in the United States. In the Asia-Pacific, Akebia quinata (Thunb.) Decne., Akebia trifoliata Koidz. var. australis (Diels) Rehd., and Stauntonia hexaphylla Decne. are medicinal and mostly used to promote urination. Akebia quinata (Thunb.) Decne. [From Japanese, akebi = Akebia quinata (Thunb.) Decne. and from Latin, quinque = five] Physical description: It is a woody climber which grows in the geographical area spanning Mongolia, China, Taiwan and Japan. Leaves: palmate, 5-lobed, spiral and arising from perulate buds. The petiole is 3.5 cm–6 cm long and twisted. The folioles are obovate, very thin, 3.2 cm × 1.5 cm–2.2 cm×1.1 cm, and show 3–4 pairs of arching secondary nerves.The apex of the folioles is notched with a tiny tip and the base is tapered.The tertiary nerves are showy below the blade and form some curled patterns. The inflorescences are racemes of about Common name: Chocolate vine, mu tong (Chinese).

Uses: Akebia quinata (Thunb.) Decne. is used mainly to promote urination and treat fever. In China, the wood of Akebia quinata (Thunb.) Decne. is used to promote sweating, digestion, milk secretion and menses, to treat fever, relieve the bowels from costiveness, to resolve inflammation, and to invigorate health. The stalks and fruits are used to expel impurities. The plant is used to treat rheumatism, lumbago, hernia, dropsy, cold and diabetes, to resolve inflammation of the stomach and kidneys, and to assuage headache. In Cambodia, Laos and Vietnam, the plant is used to invigorate health. The pharmacological potential of Akebia quinata (Thunb.) Decne. remains unexplored. The plant contains saponins (Fujita M et al., 1974) which might be involved in the uses mentioned above.

Subclass Magnoliidae

63

5 cm long. The flowers are unisexual, and Berberis-like. The perianth is red, with 3 mm × 2 mm and elliptic lobes. The andrecium includes 6 stamens of 2 mm long (Fig. 38). Reference Fujita M, et al. (1974) Yakugaku Zasshi 94(2): 194–198.

Warning: Caution must be taken as the toxic effects of this plant are unknown and products containing this plant may therefore be hazardous. Note that Akebia quinata (Thunb.) Decne products are often falsified with the Aristolochia species which are toxic to the kidneys.

Fig. 38. Akebia quinata (Thunb.) Decne. From: KLU Herbarium 10063. Ex. Herbario Universitatis Imperialis Tokyoensis. Field Collector and botanical identification. H. Kanai, 16 May 1965, Geographical localization Ohira, at the N. foot of Mt. Mishotai, Minamitsuru-Gun, Pref.: Yamanashi, Japan.

4. Family MENISPERMACEAE A. L. de Jussieu 1789 nom. conserv., the Moonseed Family. Physical description: The family Menispermaceae consists O O of 70 genera and about 400 species of tropical climbers so far known to elaborate bitter sesquiterpenes, diterpenes and O benzylisoquinoline and aporphine alkaloids. In a field collecOH tion, Menispermaceae can be recognized by cross sections of the stems showing broad medullary rays, a bright yelO O low wood and seeds which are shaped like horseshoes. The leaves are simple, alternate, simple and without stipules. The petiole is often long and thin and the blade is often cordate. Picrotoxinin The flowers are tiny, unisexual, dioecious, and actinomorphic. In the male flowers, the sepals are tiny, in 2–4 series, imbricate, the outer smaller. The petals if present, are smaller than the sepals and the anthers are short. In the female flowers, the gynecium comprises of 3–6 carpels, which are free, sessile and contain a single ovule attached to the ventral suture. The fruits are drupaceous. Pharmaceutical interest: Sesquiterpenes: A classical example of Menispermaceae is Anamirta paniculata Coleb. (Levant berries), the seeds of which

64

Division MAGNOLIOPHYTA

contain a toxic substance known as picrotoxin or cocculin. Picrotoxin is a mixture of picrotoxinin and picrotin. Picrotoxinin is a sesquiterpene specific GABAA receptor blocking agents which impede the GABAergic presynaptic inhibition of excitatory transmission of primary afferent neurones of the spinal cord (Fig. 38). Picrotoxin is toxic and as little as 20 mg induces epileptiform convulsions, myosis, and dyspnea with more or less prolonged apnea. Picrotoxin (British Pharmacopoeia, 1963), has been used in the treatment of barbiturate poisoning (3 mg–6 mg, intravenously) in Western medicine. Isoquinoline alkaloids: A number of Fig. 39. Picrotoxin blocks the GABA receptors Amazonian tribes use the extract (GP). ENM: excitatory neurone membrane, Glu: of Chondrodendron, Curarea, Sci- glutamic acid, K: ketoacid, GNT: GABAergic adotenia, Abuta, Telitoxicum, and neurone terminal, GS: GABAergic synapse, M: mitochondria, O: oxoglutamic acid, S: succinic Cissamplelos species to make arrow- semialdehyde.When a pair of GABA molecules poisons or curares. These curares bind to their sites, the receptors open and consist of bisbenzyltetrahydroisoqui- let Cl− ions enter the neurone. The resulting nolines alkaloids such as (+)-tubocu- hyperpolarization activates the sodium chanrarine, (+)-isochondrodendrine, (−)- nels responsible for neurone activation. curine, and (+)-chondrocurine which block competitively acetylcholine at nicotinic receptors at the neuromuscular junction hence causing complete relaxation of skeletal muscles and death by asphyxia. (+)-Tubocurarine which has been used to relax muscles in surgical anaesthesia (Tubocurarine Chloride, British Pharmacopoeia, 1963). Several Menispermaceae are used to promote appetite and digestion because of their bitterness which is attributed to sesquiterpenes. The dried transverse OCH3 H3C N H3C

H

O

OH

H O

OH

H3CO

(+) - Tubocurarine

N

CH3

Subclass Magnoliidae

65

slices of roots of Jateorrhiza palmata Miers (Calumba, British Pharmaceutical Codex, 1954) were used to treat atonic dyspepsia whereas the dried stems of Tinospora cordifolia (Tinospora, Indian Pharmaceutical Codex) were used to promote digestion and appetite in the form of an infusion. Weight loss phytopharmaceuticals containing Stephania tetrandra S. Moore are banned on account of their hazardous effect on the kidneys. Approximately 40 species of plants classified within the family Menispermaceae are used for medicinal purposes in the Asia-Pacific, particularly to promote urination and menses, to relieve gastrointestinal troubles, to treat fever, asthma, paralysis, rheumatism, to wash inflamed eyes, to assuage pain and to invigorate health. One might have noticed that the convulsions provoked by picrotoxin could be antagonized by the muscle-relaxing effect of bisbenzyltertrahydroquinoline alkaloids, confirming thereby the Asian belief that a poison and its antidote are inhabited in different parts of the same plant. Fibraurea chloroleuca Miers [From Greek, khloros = green and leukos = white] Physical description: It is a climber found in the rocky primary forests of the Asia-Pacific. The wood is yellow, the bark is fissured, and the medullary rays are broad in transversal section. Leaves: simple, spiral and without stipules. The petiole is 2.2 cm–5.2 cm long and keeled at both ends and twisted at the base. The blade is 8.5 cm–14.5 cm × 5.2 cm– 4 cm, leathery, oblong, elliptic, and shows 3 nerves. The apex is acuminate. The inflorescences are long and pendulous panicles. The flowers are sweetly-scented and small. The fruits are yellow-orange, elliptic and smooth Fig. 40. Fibraurea chloroleuca Miers. 3.5 cm–4 cm long drupes (Fig. 40). Synonymy: Fibraurea tinctoria Lour. Common names: Fibraurea; balet, binak (Kenyah); peron (Indonesia); bintang habu, merkunyit (Malay); huang teng (Chinese); hoang dang (Vietnamese); kam-phaeng (Thailand).

From: KLU Herbarium 29771. Flora of Sarawak, University of Malaya Herbarium. Field collector & botanical identification: Chin See Chung, 21 July 1977. Geographical localization: behind house on hill and ridge 500–1000 ft, Long Selatong Ulu, upper Buram. From: KLU 11647. Flora of Malaya. Field collector & botanical identification: Benjamin C Stone, Tanjong Keruing.Tasek Bera, 27 July 1970, Malaysia.

66

Division MAGNOLIOPHYTA

Pharmaceutical interest: It will be Uses: In Indonesia, Fibraurea interesting to learn whether the antidichloroleuca Miers is used to soothe abetes, anti-inflammatory and antisepinflamed eyes, remove blood from tic properties of Fibraurea chloroleuca feces and to assuage headache. In Miers are attributed to isoquinoline Malaysia, the plant is used to aid recovery from childbirth, treat alkaloids such as berberine and paldiabetes, and to heal ulcerated noses. matine. Berberine acts through the The plant is used to produce a delay of the onset or progression of yellow dye. diabetic complications in the eyes and other major organ systems via inhibition of aldose reductase (Lee HS, 2002). Berberine and palmatine possess significant and dose-dependent anti-inflammatory, antinociceptive and antipyretic activity (Kupeli E et al., 2002). References Kupeli E, et al. (2002) Life Sci 72(6): 645–657. Lee HS. (2002) J Agric Food Chem 50(24): 7013–7016.

Warning: Caution must be taken as the toxic effects of this plant are unknown. Pericampylus glaucus (Lamk.) Merr. [From Greek, kampulos = curved and from Latin, glaucus = glaucous] Physical description: It is a climber found in India, Southeast Asia and China which forms some kind of glaucous bunches in secondary growths and by the roadside. The stems are slender, terete and velvety. Leaves: simple, spiral and without stipules. The petiole is velvety, 2 cm–4 cm long. The blade is papery, cordate, velvety underneath, 2.9 cm × 3.1 cm–5.5 cm × 6 cm, and glaucous or yellowish. The apex is round, the base is flat or cordate, and the margin is crenate. The blade shows 3–5 pairs of secondary nerves which are visible

Fig. 41. Pericampylus glaucus (Lamk.) Merr.

Subclass Magnoliidae

above. The inflorescences are long and thin, pendulous, and axillary racemes of about 3 cm–5 cm long. The flowers are tiny and fragrant. The fruits are glaucous berries of 6 mm–7 mm diameter, each containing a horseshoe-shaped, 3 mm×5 mm spiny seed (Fig. 41).

67

Synonymy: Pericampylus formosanus auct. non Diels, Cocculus glaucus DC. Common name: Pericampylus; celuru (Indonesian).

Uses: In Indonesia, Pericampylus

Pharmaceutical interest: The pharglaucus (Lamk.) Merr. is used to counteract hair loss and to resolve macological potential of Pericampylus swelling of the spleen. In Malaysia, glaucus (Lamk.) Merr. remains unexthe plant is used to treat fever, cough, plored. This plant is known to proheadache and asthma. In Philippines, duce some alkaloids and triterpenes the juice of the roots is used to such as epifriedelinol and daucoscounteract snake-poisoning. terol (Liang P et al., 1998; Tomita M et al., 1967). The anti-hair loss, antiinflammatory and antipyretic properties of this plant are most probably due to isoquinoline alkaloids. Note that norreticuline and reticuline, benzyltetrahydroisoquinoline alkaloids common in the Ranunculales, stimulate the proliferation of cultured cells from the murine hair apparatus and stimulate mouse hair regrowth (Nakaoji K et al., 1997). What is the mechanism involved here? α-receptors? References Liang P, et al. (1998) Chung Kuo Chung Yao Tsa Chih 23(1): 39–40. Nakaoji K, et al. (1997) Biol Pharm Bull 20(5): 586–588. Tomita M, et al. (1967) Yakugaku Zasshi 87(3): 315–316.

Warning: Caution must be taken as the toxic effects of this plant are unknown. F. Order PAPAVERALES Cronquist 1981 The order Papaverales consists of 2 families of herbaceous plants, the Papaveraceae and Fumariaceae. This order is thought to have originated from the order Ranunculales, from which it inherits the ability to elaborate several sorts of isoquinoline alkaloids (Appendix I). An interesting feature of this order is the production of isoquinoline alkaloids of therapeutic value. Morphine from Papaveraceae is an instance of such an alkaloid.

68

Division MAGNOLIOPHYTA

1. Family PAPAVERACEAE A. L. de Jussieu 1789 nom. conserv., the Poppy Family Physical description: The family Papaveraceae consists of 25 genera and 200 species of laticiferous herbs or shrubs, occurring mainly in the temperate and tropical parts of the North Hemisphere. The leaves are simple, alternate, spiral and without stipules.The blade is often dissected.The flowers are showy, large, perfect, regular, and hypogynous. The calyx comprises of 2–4 caducous sepals and the corolla consists of 4–16 petals which are very thin, crumpled, brightly coloured, and imbricate.The andrecium is made of numerous stamens originating in a centripetal sequence. The anthers are tetrasporangiate and dithecal. The gynecium consists of 2–many carpels which are united to form a superior, unilocular ovary which encloses several ovules attached to parietal placentas. The stigma is flat, lobed and discoid. The fruits are capsular, containing numerous tiny seeds. Pharmaceutical interest: A classical example of Papaveraceae is Papaver rhoea L. (corn poppy, red poppy) which grows wild in Europe and the petals of which (Red-Poppy, British Pharmaceutical Codex, 1949) have been used in the form of syrup to color and sweeten pharmaceutical mixtures. Of great interest in this family are the neuroactive isoquinoline alkaloids such as morphine, codeine and papaverine present in opium, i.e. the latex of Papaver somniferum L. (Fig. 42). Opium (from the Greek opos = juice) was known of the Babylonians (4000 BC), and it was used to pacify children in ancient Egypt before 2000 BC. The Greeks and Romans used it to induce sleeping. Arabian traders introduced opium to China, and it first appeared in Chinese medical text in about AD 1000, as a treatment for diarrhea. At the end of the Middle Age, the Swiss physician Paracelsus had such a high opinion of opium that he named preparations containing it laudanum (from Latin laudare = to praise). Another example of Papaveraceae is Sanguinaria canadensis the dried rhizome of which (Sanguinaria, British Pharmaceutical Codex, 1934): has been used as an expectorant in chronic bronchitis, HO H3CO usually as a tincture (1 in 10; dose 1 mL). Argemone O O mexicana L., Chelidonium N CH3 majus L., Papaver somN CH3 niferum L., Macleaya corHO data (Willd.) R. Br., and HO Pteridophyllum racemosum Morphine Codeine Sieb. & Zucc. are used in the Asia–Pacific to treat various Fig. 42. Examples of neuroactive isoquinoline alkaloids sorts of ailments. from Papaver somniferum L.

Subclass Magnoliidae

69

Argemone mexicana L. [From Latin, mexicana = from Mexico] Common names: Mexican poppy, thistle root, prickly poppy, thornapple; khyaa (Burmese); lao chou li (Chinese); cardo santo, figo do inferno (Portuguese); chardon benit ´ des Antilles, herbe a` femme (French); lao thu lac (Vietnamese); adormidera espinosa (Spanish); brahmadandi (Tamil and Sanskrit).

Physical description: It is a tropical shrubby herb which grows to a height of 1.2 m. The plant is native to tropical America. The stems are thorny, succulent and glabrous. The latex is yellow and slightly corrosive. Leaves: simple, glaucous, without stipules and amplexicaul. The blade is glaucous, deeply incised, 11.5 cm × 7 cm–3.5 cm × 2.5 cm, and shows 3– 4 pairs of secondary nerves. The margin is thorny. The flowers are yellow, terminal, and 4 cm in diameter. The calyx comprises of 3 prickly and ovate sepals. The corolla comprises of 6 branaceous. The ovary is prickly and ovules. The stigma is sessile and 4– 6-lobed. The fruits are prickly capsules, 2.5 cm–3.8 cm in diameter and opening by 4–6 valves. The seeds are numerous and netted (Fig. 43). Pharmaceutical interest: Chemotherapeutic properties:The antiseptic property of Argemone mexicana L. is very likely to be attributed to isoquinoline alkaloids such as sanguinarine, berberine and protopine, which abound in the plant (Santos AC et al., 1932). Sanguinarine exhibits a broad

Fig. 43. Argemone mexicana L. From: Delhi University Herbarium 004344. Flora of India. Geographical localization: Delhi ridge, Delhi, India, altitude 720 ft., Feb 1961. Field Collector: SK Avova. Botanical identification: CS Venktast.

petals which are yellow and memsingle-celled and contains numerous Uses: In Burma, the latex of Argemone mexicana L. is used to treat dropsy and the seeds are eaten to relieve the bowels of costiveness. In China, the leaves of Argemone mexicana L. are used to invigorate health, inhibit fertility and promote digestion. In Indonesia, Argemone mexicana L. is used to treat jaundice, skin affections, dropsy, blisters and ulcers, and to promote menses. In the Philippines, the flowers are used to induce narcosis and treat lung diseases.

70

Division MAGNOLIOPHYTA

panel of pharmacological activities. It is antimicroO bial, antifungal, and anti-inflammatory. It inhibits O Na+ /K+ -dependent ATPases, has a positive inotro+ pic action, and interacts with DNA. Sanguinarine N CH3 chloride is used in mouthwashes for its ability to O O bind dental plaque and to inhibit the growth of bacSanguinarine teria at a very low dose. The plant is interesting because of (+/−)-6-acetonyldihydrochelerythrine, which exhibits a significant Anti-Human Immunodeficiency Virus activity in H9 lymphocytes with EC50 and Therapeutic Index values of 1.77 µg/mL and 14.6, respectively (Chang YC et al., 2003). The acetone fraction of the petroleum ether extract of seeds from Argemone mexicana L. destroys the larvae of Aedes aegypti at doses of 200, 100, 50 and 25 ppm (Sakthivadivel M et al., 2003). The plant displays some levels of antiplasmodial activities (Adjobimey T et al., 2004). References Adjobimey T, et al. (2004) Comptes Rendus Chimie 7(10–11): 1023–1027. Chang YC, et al. (2003) Planta Med 69(2): 148–152. Dalvi RR, et al. (1985) Experientia 41(1): 77–78. Kosina P, et al. (2004) Food and Chemical Toxicology 42(1): 85–91. Santos AC, et al. (1932) J Am Chem Soc July 54: 2923–2924. Sakthivadivel M, et al. (2003) Bioresour Technol 89(2): 213–216. Sood NN, et al. (1985) Trans R Soc Trop Med Hyg 79(4): 512–515.

Warning: Sanguinarine is toxic to the liver. A single intraperitonneal dose (10 mg/Kg) of sanguinarine will boost the enzymatic activity of SGPT and SGOT and cause a significant loss of microsomal cytochrome P-450, reduce body and liver weight, induce peritoneal and hepatic edema and hepatocellular degeneration and necrosis (Dalvi RR, 1985). The seed is a common adulterant of mustard seeds. Ingestion of Argemone seed oil causes epidemic dropsy in humans in Africa and India with hyperpigmentation of the skin and sarcoidal angiomatous swellings and glaucoma. Four cases of dropsy have been reported as a result of body massages with contaminated mustard oil sanguinarine (Sood NN et al., 1985). The effects of sanguinarine and chelerythrine on pigs are also reported (Kosina et al., 2004). Chelidonium majus L. [From Greek, khelid on = swallow and from Latin, magnus = great] Physical description: It is a perennial herb which grows to a height of 40 cm. It is native to Eurasia where it grows wild on old walls, in piles of rubble and

Synonymy: Chelidonium sinense DC. Common names: Greater celandine, tetterwort, pile-wort, or rock poppy.

Subclass Magnoliidae

71

O O

O N+ H3CO H3CO

OH CH3

Chelerythrine

HOOC

O

COOH

Chelidonic acid

in ditches. The plant is laticiferous and the latex is orange and caustic. The stems are succulent and glaucous. Leaves: pinnate, without stipules, 14 cm– 9 cm × 5 cm–4.7 cm and alternate. The margin of the blade is crenate. The flowers are showy and terminal. The corolla comprises of 4 petals which are yellow and membranaceous. The andrecium consists of numerous stamens. The ovary is fusiform. The fruits are fusiform capsules containing numerous seeds (Fig. 44). Uses: In China and Japan, Chelidonium majus L. is used to heal stomach ulcers. In Korea, Chelidonium majus L. is used to treat gastric cancer.

Pharmaceutical interest: Anti-cancer properties: Chelidonium majus L. elaborates several sorts of cytotoxic isoquinoline alkaloids such as chelidonine, chelerythrine, sanguinarine, berberine, coptisine and stylopine which are probably involved in the anti-cancer property mentioned above. NSC-631570 (Ukrain) is a semisynthetic compound of thiophosphoric acid and chelidonine which nearly doubles the median survival times of patients with histologically proven unresectable pancreatic cancer (Gansauge F et al., 2002). The anti-cancer property of this plant can

Fig. 44. Chelidonium majus L. From: KLU Herbarium 26739. Herb. Lugd. Batav. Field collector & botanical identification: JF Maxwell, 17 May 1977. Geographical localization: Leiden, Netherlands. Erect herb growing around the RijksHerbarium.

72

Division MAGNOLIOPHYTA

also be mediated by glycoproteins such as a CM-Ala, a protein-bound polysaccharide which enhances nitric oxide production in peritoneal macrophages and exhibits antitumoral activity, suggesting antitumoral immunostimulator properties (Song JY et al., 2002). Anti-ulcer property: One might set the hypothesis that the medicinal uses mentioned above results from isoquinoline alkaloids with anticholinergic effect. Note that an extract of Chelidonium majus reduces gastric acid output, increases mucin secretion, and boosts the release of prostaglandin E2 , and leukotrienes (Khayyal MT et al., 2001). References Gansauge F, et al. (2002) Langenbecks Arch Surg 386(8): 570–574. Khayyal MT, et al. (2001) Arzneimittelforschung 51(7): 545–553. Song JY, et al. (2002) Arch Pharm Res 2002 Apr 25(2): 158–164.

Warning: The juice can produce congestion of the lungs and liver, and narcosis. Skin poisoning results from the handling of the crushed plant. The corrosive property of the latex of Chelidonium majus L. and of several other plants classified within the family Papaveraceae is partially attributed to a quinone, chelidonic acid.

2. Family FUMARIACEAE A. P. de Candolle 1821 nom. conserv., the Fumitory Family Physical description: The family Fumariaceae consists of about 20 genera and 400 species of poisonous perennial herbs, growing mainly in the Northern temperate regions and in South Africa. The stems are often slender and juicy. The leaves are simple, alternate or subopposite, without stipules and often dissected. The inflorescences are cymose or racemose. The flowers are perfect, zygomorphic, and hypogynous.The calyx comprises of a pair of small and deciduous sepals, and the corolla consists of 4 petals.The petals are imbricate, the outer 2 often saccate or spurred at the base, and the inner 2 narrower and sometimes coherent to the apex. The andrecium consists of 4 free stamens facing the petals, or 6 stamens united in 2 bundles. The gynecium comprises of a pair of carpels united to form a compound and unilocular ovary, containing a pair of anatropous ovules attached to the parietal placentas. The style is long and thin, and the stigma is lobed. The fruits are capsular. The seeds are glossy, crested or nude. Several handsome garden plants belong to family Fumariaceae, most notably, Dicentra spectabilis (L.) Lemaire (bleeding heart) and Dicentra cucullaria (L.) Bernh. (Dutchman’s breeches). Pharmaceutical interest: The dried tubers of Dicentra canadensis (squirrel or turkey corn) and Dicentra cucullaria (L.) Bernh. (Corydalis, British

Subclass Magnoliidae

73

Pharmaceutical Codex, 1934) have been used to invigorate and to promote urination (dose 0.3 g–1 g) in Western medicine. Isoquinoline alkaloids: Corydalis, Dicentra and Fumaria species are toxic on account of isoquinoline alkaloids such as bulbocapnine, protopine, and bicuculline. Bulbocapnine is a dopaminergic antagonist which has been used as a sedative in postencephalitic conditions, Meni ´ ere’s ` syndrome, and for tremors of various origins (dose 100 mg, orally or subcutaneously, once or twice daily). Protopine, is the principal alkaloid of jaundice herb or Fumaria officinalis L. (Common fumitory,French Pharmacopoeia, 10th edition) which has been used to treat liver disorders and to invigorate. This protoberberine is spasmolytic, anticholinergic, antiarrhytmic, antibacterial and increases the binding of γ aminobutyric acid to its central receptor. Bicuculline, like picrotoxin, is a specific GABA receptor blocking agent which impedes the GABAergic presynaptic inhibition of excitatory transmission of primary afferent neurones of the spinal cord resulting in epileptiform convulsions, myosis, and dyspnea with more or less prolonged apnea (Fig. 45). Approximately 20 plants classified within the family Fumariaceae, including Corydalis incisa (Thunb.) Pers., are mostly used in the Asia-Pacific to assuage pain, counteract putrefaction of the skin and to heal hemorrhoids. O NH2

N

O

HO

HO

HO

H3CO

Dopamine

CH3

Bulbocapnine (dopaminergic antagonist) O N +

N

O O

O

O O

O Protopine (cholinergic antagonist)

Acety lcholine O O

N

CH3

O HO

O

NH2 O

γ - Aminobutyric acid (GABA)

O O Bicuculline (GABAergic antagonist)

Fig. 45. Note the similitude of chemical structure of bulbocapnine, protopine and bicuculline with dopamine, acetylcholine and γ -aminobutyric acid.

74

Division MAGNOLIOPHYTA

Corydalis incisa (Thunb.) Pers. [From Greek, korudallis = crested lark and from Latin, caedere = cut]

Common name: Murasaki keman (Japanese).

Physical description: It is a herb which grows to a height of 30 cm. It is found Uses: In China, the flowers of in Korea, Japan and China. The stems Corydalis incisa (Thunb.) Pers. are succulent, smooth and glabrous. The are used to treat prolapse of the roots are fibrous. Leaves: simple, alterrectum, and a decoction of the nate, 5.5 cm × 1.2 cm–6 mm × 3 mm, plant is applied externally to counteract skin putrefaction and to cauline, and incised. The petiole is heal piles. 10 cm–1.3 cm × 1 mm and forms a sheath at the base. The inflorescences are terminal racemes. The flowers are reddish-purple, 1.7 cm–1.4 cm long and tubular. The flower pedicels are 5 mm–1 cm long. The fruits are 8 mm–9 mm × 1 mm fusiform capsules (Fig. 46). Pharmaceutical interest: It will be interesting to learn whether the medicinal properties of Corydalis incisa (Thunb.) Pers. are attributed to benzo[c]phenanthridine alkaloids such as corynoline, acetylcorynoline, corynoloxine, luguine, 6-oxocorynoline, and 12-hydroxycorynoloxine (Naruto S et al., 1968; Kim DK et al., 2000). Corynoline inhibits the enzymatic activity of acetylcholinesterase dose-dependently, in a reversible and noncompetitive manner, with an IC50 value of 30.6 µM. (Kim DK et al., Fig. 46. Corydalis incisa (Thunb.) Pers. From: 2002). Benzo[c]phenanthridine alka- KLU Herbarium 17912. Ex. Herb Universiloids are very interesting because tatis Tokyoensis. Field collector & botanical they inhibit the enzymatic activ- identification: Y Tateishi, 11 Apr 1971. Geoity of topoisomerase in cancerous graphical localization: Japan, Tokyo, Kiyose, cells. Are corynoline, acetylcorynoline, altitude 50 m. corynoloxine, luguine, 6-oxocorynoline, and 12-hydroxycorynoloxine able to inhibit the enzymatic activity of topoisomerase? References Kim DK, et al. (2000) Arch Pharm Res 23(6): 589–591. Kim DK, et al. (2002) Arch Pharm Res 25(6): 817–819. Naruto S, et al. (1968) Tetrahedron Lett 14: 1705–1709.

Warning: This herb is very poisonous.

Subclass Hamamelidae

75

II. Subclass HAMAMELIDAE Takhtajan 1966 The subclass Hamamelidae consists of 11 orders and 24 families, and about 3400 species of plants which are thought to have originated from some tanniferous Magnoliidae, forced to adapt to a climate of alternating wet and dry seasons in the Upper Cretaceous (Appendix I). These are mostly trees, the flowers of which are tiny, packed in spikes, unisexual, with distinct carpels, and adapted to wind pollination. In this Subclass, the use of alkaloids as chemical weapons has dramatically declined with the advent of tannins and flavonoids. The mechanisms by which tannins impede microbial infestation are enzyme inhibition, substrate deprivation, action on membranes, and metal ion deprivation. When consumed by mammalian, tannins form complexes with salivary glycoproteins and rend the plant unpalatable. Levels of tannins above 5% of the diet induce hemorrhagic gastroenteritis, necrosis of the liver, and kidney damage with proximal tuberal necrosis and death. Proanthocyanidins or condensed tannins (non-hydrolysable) are not absorbed by the digestive tract, but damage the mucosa of the gastrointestinal tract, and decrease the absorption of nutrients. Tannins explain the astringent properties of these plants. Urticales is the largest and oldest order in this subclass.

A. Order URTICALES Lindley 1833 The order Urticales consists of 6 families and 2200 species of trees, shrubs, climbers and herbs, which have evolved from the Hamamelidales where it inherited the ability to elaborate interesting series of prenylated flavonoids.

1. Family CANNABACEAE Endlicher 1837 nom. conserv., the Hemp Family Physical description: The Cannabaceae family consists of 2 genera and 3 species of herbs known to produce prenylated flavonoids. The leaves in this family are opposite, alternate, palmately lobed (Humulus) or palmately compound (Cannabis) and stipulate. The flowers are tiny and either male or female. The male flowers are paniculate and comprise of a calyx made of 5 imbricate sepals, with 5 stamens facing the sepals. The anthers are erect in buds, 2-locular, and open lengthwise. The female flowers are sessile, crowded or strobilate, with large showy bracts. The calyx envelops the ovary which is sessile, 1-locular and contains a single pendulous ovule. The style is central and 2-lobed. The fruits are achenes, covered with a persistent calyx. Pharmaceutical interest: The dried strobiles of Humulus lupulus L. (hops, British Pharmaceutical Codex, 1934) are aromatic, bitter and mildly sedative,

76

Division MAGNOLIOPHYTA

considering its 2-methyl-3-buten-2-ol, and are used to prepare beer. Cannabis sativa subsp. sativa is cultivated for fiber (hemp) and Cannabis sativa subsp. indica (Lam.) Small & Cronq. is cultivated principally for psychotropic drugs (marijuana, hashish). Cannabis sativa L. [Probably from Hebrew, kaneh bosem = aromatic reed, in Exodus 30:23, and refer to the recipe for the Holy Anointing Oil of Israel and from Latin, sativus = cultivated]

Synonymy: Cannabis sativa subsp. indica (Lam.) Small & Cronq. Common names: Cannabis, hemp, ganja ´ (Tamil); vijaya, indrasana (Sanskrit).

Physical description: It is a shrubby herb which grows to a height of 3 m. The plant grows wild in India and Pakistan. The stems are terete and hairy. Leaves: at the base of the stem the leaves are opposite and palmately lobed. At the apex of the stems the leaves are 1- or 3-foliolate. The petiolules are very short and channeled. The blade is hairy underneath, 10.5 cm–6 cm × 1.1 cm–6 mm, and papery. The margin is serrate. The midrib and secondary nerves are sunken above and raised below, and the blade shows 6–10 pairs of secondary nerves. The male flowers are grouped in panicles. The female flowers are grouped in compact cymes mixed with foliaceous bracts.The flowers are tiny and 5-lobed. The fruits are ovoid achenes (Fig. 47). History and uses: Cannabis has been cultivated for its seeds and fibers from a very remote period in time, but its narcotic properties are usually not marked in plants grown in temperate regions, and even in India, an active drug can only be grown in certain districts. Cannabis sativa L. was valued as long ago as 6000 BC in China where the seeds were used for food. The Assyrians used it as incense, and in India and Africa, the

Fig. 47. Cannabis sativa L. From: Herbarium KLU 14958. Field collector & botanical identification: Benjamin C Stone. Geographical localization: Phoenchit, Thailand (Peninsula).

Subclass Hamamelidae

77

drug was used in religion and magic, and activities requiring endurance or physical effort. Greeks were acquainted with hemp more than 2000 years ago. Herodotus mentioned that in 600 BC, the Scythians burned its seeds to produce a narcotic smoke. Dioskurides mentioned that if the seeds of cannabis were eaten too freely, they destroyed virility, and that the juice was used to relieve earache. The earliest medical writer who distinctly mentioned the intoxicating properties of cannabis is Ibn Baitar, a native of Africa who died in Damascus in 1248. Galen asserted that in his time (Middle Ages), it was customary to give hemp seeds to the guests at banquets in order to promote hilarity and enjoyment (Lib.I, De Aliment. Facult.). Georg Everhardus Rumphius, a Dutch naturalist who lived in Indonesia during the 17th century, stated that the kind of mental excitement produced by hemp depended upon the temperament of the consumer. M Rouyer, apothecary to Napoleon and a member of the Egyptian Scientific Commission, noted that leaves and tops collected before ripening were used by Egyptians to prepare a conserve (Bulletin de Pharmacie, 1810, p 400). The British physicians of the army of India (Dr O’ Shaughnessy) and Bonaparte’s expedition to Egypt shared the same responsibility for the introduction of cannabis into Europe in the 19th century. It was consumed in intellectual circles and the illicit use of cannabis spreaded rapidly. Cannabis (British Pharmaceutical Codex, 1949) consists of the dried flowering or fruiting tops of the male Cannabis sativa L. It has been used to assuage migraine and headache due to hypertension. Three main types of narcotics are produced from the flowering tops, leaves, hairs and resin OH of Cannabis sativa L.: marihuana, Indian form and hashish. Marihuana consists of a mixture of the dried, crushed flowers, leaves and smaller stems. It is used for smoking, generally in the O form of cigarettes, either alone or mixed with tobacco (joints).The name marihuana is thought ∆9-Tetrahydrocannabinol to have orginated from the Spanish word marijuana which is a low grade of tobacco. The Indian forms consist of 3 main types of preparations of Cannabis sativa L. bhang, ganja ´ and charas. Bhang consists of the dried leaves and flowering shoots of male and female plants. Ganja ´ consists of the dried flowering tops of the female plant harvested when coated with resinous exudate. Charas or churrus consists of hairs, resin and fragments of leaves collected from the flowering tops and leaves. Hashish corresponds to first grade charas and lower grade ganja. The name hashish comes from the name of hashishin, followers of Hasan ibn al-Sabbah (11th century Persian sect), who committed political murders throughout Asia Minor in return

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for cannabis resin. The effect of hashish was described as early as the middle of the 19th century in the literary writing of Baudelaire as follows : “External objects, one by one, slowly assume peculiar appearances. . . Sounds put on colors, and colors put on music. . . your personality disappears. . . you will feel yourself evaporating. . . But you should see the results. . . hashish annihilates, hashish is a suicide weapon. . . will isolate you. . . it is for idle bastards. Hashish is useless and dangerous” (Les Paradis Artificiels, Garnier-Flammarion, 1966, Paris). In Burma, cannabis is used to treat tetanus. In China, the seeds are used to invigorate health, stop vomiting, counteract putrefaction of the skin, promote menses and urination, relieve the bowels of costiveness, resolve inflammation, expel intestinal worms and to induce narcosis. In Vietnam, the plant is used to assuage rheumatic pains, headache and stomachache. The seeds are used to treat uterine prolapse and fever. Pharmaceutical interest: Cannabinoids: The chemical constituents and pharmacological effects of Cannabis sativa L. are well-known and thousands of references are available on these subjects. Among the hundreds of different compounds reported are a group of terpenophenolic substances known as cannabinoids. The narcotic principle of Cannabis sativa L. is a cannabinoid known as 9 -tetrahydrocannabinol (9 -THC) which is absent from the seeds and stems and present in the leaves and resin. 9 -THC is lipophilic and binds to specific receptors located in the brain. The effects, pleasant or frightening, of 9 -THC depend on the dose, the route of administration and the personality of the user. An oral dose of 50 µg/Kg–200 µg/Kg of 9 -THC produces euphoria, a feeling of well-being, hilarity and peace. An oral dose of 240 µg/Kg of 9 -THC produces a change in auditory and visual perception. An oral dose of 300 µg/Kg–480 µg/Kg of 9 -THC produces visual and auditory perception hallucinations. Loss of concentration, anxiety, panic, drowsiness, lethargy and sleepiness occur after a single oral dose of 0.4 mg/Kg–1 mg/Kg. Clinical trials have confirmed the antiemetic activity of 9 -THC orally. It is marketed in the United States, in capsules of 2.5 mg, 5 mg, and 10 mg (Marinol® ). 9 -THC and structural analogs could possibly be developed as drugs to treat glaucoma and asthma, to stop convulsions and spasms, and to assuage pains. Reference Hurd YL, et al. (2004) Neurotoxicology and Teratology In Press, Corrected Proof, Available online 8 December 2004.

Warning: Marijuana impairs growth in the mid-gestation fetuses (HurdYL et al., 2004).

Subclass Hamamelidae

79

Humulus scandens (Lour.) Merr. [From Latin, humus = soil and scandere = climb] Physical description: It is a climber Synonymy: Humulus japonicus Sieb. native to East Asia. The stems are & Zucc. slender, terete and hairy. Leaves: simCommon name: Japanese hop. ple, opposite, without stipules. The petiole is 5 cm–7 cm long, hairy and grooved. The blade is papery, 3-lobed, 5.2 cm × 7.1 cm–2 cm × 2.5 cm and hairy. The margin is serrate, and the midrib and secondary nerves are sunkely above and raised below.The inflorescences are tiny axillary racemes.The flowers are 3 mm long. The calyx consists of 5 lanceolate sepals which are free and hairy. The petals are glabrous, yellow, lanceolate, free, and opposite to the sepals (Fig. 48). Uses: In China, the aerial parts are used to treat malaria, typhoid, gonorrhea, syphilis, cough, colds, lithiasis, spermatorrhea and malignant sores, promote urination, invigorate the genito-urinary system, stop dysentery and to resolve inflammation. The fruit is used to treat fever, promote appetite and urination, stop dysentery and to counteract poisoning from snake bites and scorpion stings. In Vietnam, the leaves are used to treat fever and stop dysentery.

Pharmaceutical interest: Inhibition of Cytochrome P450 : To date, the therapeutic potential of Humulus scandens (Lour.) Merr. remains unexplored. A number of flavonoids isolated from Humulus lupulus L. (hop), inhibit potently and selectively the human cytochrome P450 which is responsible for steroid metabolism and microsomal oxidative

Fig. 48. Humulus scandens (Lour.) Merr. From: KLU Herbarium 042729. Field collector & botanical identification: Luo Lin-bo, 20 Aug 1994. Geographical localization: Hunan, China, Xining Co., 26◦ 4 North–110◦ 8 East, altitude: 320 m.

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system (Henderson MC et al., 2000). Such flavonoids could be responsible for the possible diuretic, hormonal and anti-malignant properties of Humulus scandens (Lour.) Merr. Cytochrome P450 is involved in the electron transport necessary for the 11-hydroxylation of cholesterol into aldosterone which is a steroid hormone that inhibits urination. Metapyrone is an example of a diuretic drug which acts by inhibiting 11-hydroxylation of the steroid nucleus. Three flavonoids, xanthohumol, dehydrocycloxanthohumol and isoxanthohumol, isolated from hop inhibit dose dependently (0.1 µM–100 µM) the proliferation of human breast cancer (MCF-7), colon cancer (HT-29) and ovarian cancer (A-2780) cultured in vitro (Miranda CL et al., 1999). It will be interesting to learn whether a more intensive future research on Humulus scandens (Lour.) Merr. will disclose any molecules of chemotherapeutic interest. Hops is well-known to be estrogenic owing to the phytoestrogens 8-prenylnaringenin (8OH isopentenylnaringenin) which binds to estrogen receptors (Milligan SR et al., 2000). One O might set the hypothesis that an estrogenic HO mechanism would explain the use of Humulus scandens (Lour.) Merr. to invigorate the genital system and to impede spermatorrhea. EstroOH O gens act on the hypothalamus to inhibit the 8 - Isopentenylnaringenin release of FSH which stimulates spermatogenesis. In addition, estrogen also inhibits the release of ICSH (LH), thereby decreasing testosterone production and inhibiting libido. References Henderson MC, et al. (2000) Xenobiotica 30(3): 235–251. Milligan SR, et al. (2000) J Clin Endocrinol Metab 85(12): 4912–4915. Miranda CL, et al. (1999) Food Chem Toxicol 37(4): 271–285.

Warning: Carcinoma of the breast is often dependent on estrogen. Most of the breast tumors occur in premenopausal women, in whom there is excess estrogen, and concern must be expressed regarding the unrestricted use of estrogenic herbal products.

2. Family MORACEAE Link 1831 nom. conserv., the Mulberry Family Physical description: The family Moraceae consists of about 40 genera and 1000 species of trees, shrubs, climbers and herbs. Moraceae are laticiferous and contain prenylflavones, and cardenolides (Antiaris, Antiaropsis, Castilla).

Subclass Hamamelidae

81

The leaves are simple, stipulate, often thick, large and glossy. The stipules often form a cap over the leaf buds. The flowers are tiny, packed in compact axillary inflorescences and comprise of 4–5 sepals and stamens, and 2 free carpels each containing 1 ovule.The fruits are syncarps or drupes. An example of Moraceae is Ficus benjamina L. (weeping fig). Other examples are Morus alba L. (mulberry), Ficus elastica Roxb. (India rubber plant), Castilla elastica Cerv. (caoutchouc), Artocarpus communis Forst. (bread-fruit), Artocarpus heterophyllus Lam. (jack-fruit) and Ficus carica L. Pharmaceutical interest: Mulberry (British Pharmaceutical Codex, 1934), consists of the ripe fruits of Morus alba L. which have been used to relieve the bowels of costiveness, to promote expectoration and as adjuvant in the form of syrup (Mulberry syrup, dose 2 mL–4 mL) prepared by dissolving sucrose in the expressed juice. The latex of Ficus species is often used to heal wounds, remove warts, assuage toothache, and to treat skin infection. This could be due to the fact that the latex often contains mixtures of papain-like proteases (ficin), which could be used therapeutically to expel worms or to resolve inflammation, and in the food industry to tenderize meat. The therapeutic potential of this large family is not fully known til to date. Prenylflavones and lectins of Moraceae represent an interesting reserve field of chemotherapeutic investigation and should be worth being assessed further for their cytotoxic and/or antiviral properties. About 50 species of plants classified within the family Moraceae are used for medicinal purposes in the Asia-Pacific. These are mostly used to treat fever, heal wounds, assuage stomachache, promote the secretion of milk, and to stop diarrhea and bleeding. Antiaris toxicaria Lesch. [From Malay, antjar = Antiaris toxicaria Lesch. and from Greek, toxikon = poison for arrow] Physical description: It is a lowland Common names: Upas tree; pokok rainforest tree which grows to a height ipoh (Malay); upas (Javanese). of 45 m. It is found in Malaysia, Indonesia, India and South China. The bark is dark grey. The inner bark is yellowish with a milky latex. The wood is white and soft. The stems are hairy at the apex. Leaves: simple, alternate and stipulate. The petiole is 2 mm–1 cm long. The blade is oblong-elliptic, and 7.5 cm–20 cm × 3.6 cm–8.5 cm. The apex of the blade is pointed, and the base is round and asymmetric.The inflorescences are axillary. The male flowers are tiny and consist of a 4-lobed perianth and 8 stamens. The female flowers show a pair of styles. The fruits are pear-shaped, pulpy, tomentose and crimson drupes (Fig. 49).

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The plant is used for medicinal purposes in India, where the latex is ingested in very small doses to stimulate blood circulation and the heart. In Malaysia, Dayaks and Ibans use the latex to heal wounds, and to counteract snake-poison. In the Philippines, the leaves and bark are used to treat fever and to stop dysentery. Pharmaceutical interest: Cardiovascular properties: The toxic principles of Antiaris toxicaria Lesch. are cardiac glycosides (Chen KK et al., 1983) which bind to the Na+ , Uses:This plant is the “Arbor Toxicaria” of Georgius Everhardus Rumphius (1628–1702), who wrote in Thesaurus Amboinensis that “everything perishes that its wind touches, as so too do all animals shun it when they pass this tree, while the birds fly over”. Although it is a little exaggerated, the plant is dreadfully toxic. The latex of Antiaris toxicaria Lesch. has been used in the Asia-Pacific either alone or mixed with the juice of Strychnos (see p.), Amorphophallus, Dioscorea, Lophopetalum or Derris, to make arrow and dart poison, and occasionally for judicial sentence. The process of getting the arrow-poison has been first reported by Mr L Wray (Curator and State Geologist of Perak) in the Kew Bulletin edition of October 1891 as follows: “the sap is obtained from the tree by scoring the bark and is heated on a spatula till evaporated, leaving a dark gummy substance in which the arrow is dipped. About 3 ounces and a half of sap will do for 100 arrow points”.

Fig. 49. Antiaris toxicaria Lesch.

Fig. 50. Cardenolides bind to Na+ /K+ ATPase protein (A) and inhibit therefore the active transfer of Na+ out of the sarcolemma. Na+ being in excess in the sarcolemma is transferred actively out of the sarcolemma through a Na+ /Ca2+ protein (B) which transfers meanwhile Ca2+ into the sarcolemma. Increase of Ca2+ into the sarcolemma results in stronger myofibril (M) contraction, hence stronger cardiac contraction.

Subclass Hamamelidae

83

K+ -ATPase pumps of the cardiac myocytes. In normal conditions, the contraction cycle of myocytes consists of 5 electrical events or phases, which correspond to the transfers of sodium, calcium and potassium ions through the sarcolemma transtubular membrane. The first phase, or phase 0, corresponds to a massive entry of sodium ions through fast sodium ions channels and therefore resulting in the depolarization of the sarcolemma membrane. During the phases 1, 2 and 3, or repolarization, calcium ions and sodium ions enter the cell and potassium ions leave the cells slowly. During phase 4, or diastole, sodium ions are transported out of the cell and potassium ions are transported in the cell through a transtubular Na+ / K+ -ATPase protein. The binding of cardiac glycosides to Na+ / K+ -ATPase results in an elevation of intracellular sodium which stimulates Na+ /Ca2+ exchanges, leading therefore to increased intracellular calcium and enhanced contractility of the myofibrils (Fig. 50). O O

HO Cardenolide aglycone

References Chen KK, et al. (1965) J Pharmacol Exp Ther 150(1): 53–54. Ho LM, et al. (1996) Nephron 72(4): 676–678.

Warning: The latex of Antiaris toxicaria Lesch. is reported to cause per os a fatal rhabdomyolisis and acute oliguric renal failure (Ho LM et al., 1996). The case of an occupational asthma caused by Antiaris wood has been recently reported. Artocarpus heterophyllus Lamk. [From Greek, artos = bread, karpos = fruit and heteros = different and phullon = leaves] Physical description: It is a tropical fruit tree probably native to India. The bark is dark grey and exudes an abundant milky latex when incised.

Common names: Jack-fruit; nangka (Malay); jaca (Portuguese); chakka (Malayalam).

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The stems are articulate. Leaves: simple, spiral, and stipulate. The petiole is 1.25 cm–4 cm long. The blade is elliptic to obovate, leathery, glossy, deep green on the surface, and 5 cm–23 cm × 2 cm–11 cm. The apex is blunt and the base of the blade is tapered. The flowers are unisexual, tiny and arranged in separate and axillary heads. The male flower consists of a tiny 2- to 4-lobed perianth and a single stamen. The female flowers consists of a tiny perianth tube, a single ovary sunk in the receptacle and a long style. The fruits are 30 cm–90 cm × 15 cm–30 cm, ovoid, smelly, heavy, greenish-yellow, covered with conical warts and cauliflorFig. 51. Artocarpus heterophyllus Lamk. ous. The seeds are 4 cm × 2 cm, ovoid, brownish, smooth and embedded within a thick orange gelatinous jacket which is edible (Fig. 51). Pharmaceutical interest: Antimicrobial properties: The seeds Uses: In Burma and China, the latex is of Artocarpus heterophyllus Lamk. applied to heal ulcers and abscesses. abound in lectins which have verThe roots are used to stop diarrhea. satile application in immunopharmaIn Malaysia, ashes of leaves are used cological research (Kabir S et al., to heal wounds. In the Philippines, the 1998; Hashim ON et al., 2001). One latex is used as it is in Burma, and the of these lectins inhibits in vitro the leaves as it is in Malaysia. In Vietnam, growth of Herpes Simplex Virus type 2 the wood is used to stop convulsion. A decoction of the leaves is drunk to (HSV-2), Varicella-zoster Virus (VZV), stimulate the production of milk. The and Cytomegalovirus (CMV) with IC50 sap is used to treat syphilis and to values of 2.5, 5, and 10 Eg/mL respecexpel intestinal worms. tively and stimulates NK lymphocyte (CD16(+)/CD56(+)) proliferation (Wetprasit N et al., 2000). Prenylflavones characterized from Artocarpus heterophyllus Lamk. inhibit the proliferation of cultured cariogen bacteria at 3.13 µg/mL–12.5 µg/mL (Sato M et al., 1996). Antidiabetes property: A decoction of the leaves given per os at a dose of 20 g/Kg improves glucose tolerance in normal and diabetic patients

Subclass Hamamelidae

(Fernando MR et al., 1991). This activity might be attributed to prenylflavones like cycloheterophyllin, artonin A and artonin B, which inhibit iron-induced lipid peroxydation in rat brain homogenate, scavenge 1,1,-diphenyl-2-picrylhydrazyl and peroxyl radicals, and scavenge hydroxyl radicals experimentally-generated (Ko FN et al., 1998).

OH

85

O

O O

O HO

OH

Artonin A

References Fernando MR, et al. (1991) J Ethnopharmacol 31(3): 277–282. Hashim On, et al. (2001) Immunol Invest 30(1): 21–31. Kabir S, et al. (1998) J Immunol Methods 212(2): 193–211. Ko FN, et al. (1998) Free Radic Biol Med 25(2): 160–162. Sato M, et al. (1996) J Ethnopharmacol 54(2-3): 171–176. Wetprasit N, et al. (2000) Jpn J Infect Dis 53(4): 156–161.

Parartocarpus venenosus (Zoll. & Mor.) Becc. ssp. forbesii (King) Jarret [From Greek, artos = bread, karpos = fruit, heteros = different and from Latin, venenosus = poisonous] Physical description: It is a tree Common name: Berteh paya (Malay). which grows to a height of 40 m in the lowland flooded rainforests of Uses: In Malaysia, the latex of PararMalaysia and Indonesia. The core of tocarpus venenosus (Zoll. & Mor.) the trunk is hollow and often inhabBecc. ssp. forbesi (King) Jarret is used ited by red ants. The bole is straight by the Orang Asli to make arrowThe wood is soft and whitish. The bark poison. In Indonesia, the latex is applied is ash-coloured, with large lenticels, externally to resolve inflamed parts and and papery scaly. The inner bark is to heal wounds. This plant has apparently not been investigated for its therorange-cream, and exudes an abunapeutic potential. dant and very poisonous milky latex. Leaves: simple, entire, spiral and stipulate. The petiole is 1.5 cm–4 cm long. The blade is leathery, obovate, and 6 cm–17 cm × 3.5 cm–9 cm. The blade shows 6–12 pairs of secondary nerves. The flowers are axillary, and the male heads are globose.The fruits are globose, yellowish, 18 cm in diameter, spiny and attached to the stems by 3 cm–10 cm long pedicels. Warning: This plant is very poisonous.

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B. Order FAGALES Engler 1892 The order Fagales consists of 3 families and more than 900 species of timber trees, half of which belong to the genus Quercus (oak). Fagales are mostly North Temperate and thought to have originated from the order Hamamelidales independently from Urticales (Appendix I). Tannins of Fagales are of pharmaceutical value.

1. Family FAGACEAE Dumortier 1829 nom. conserv., the Beech Family Physical description: The family Fagaceae consists of about 7 genera and 800 species of timber trees known to abound with tannins and flavonoids. The wood is hard and heavy, and of commercial value. The leaves are simple, alternate, often leathery, and stipulate. The stipules are deciduous. The inflorescences are spikes of tiny unisexual, and monoecious and anemophilous flowers. The calyx comprises of 6 small sepals. The andrecium comprises of 4–40 stamens, the anthers of which are tetrasporangiate, dithecal and opening by longitudinal slits. The gynecium comprises of 2–12 carpels united to form a compound, and an inferior ovary containing a pair of axial and pendulous ovules in each locule.The styles are free and as numerous as the carpels The fruits are acorns. A classical example of Fagaceae is Quercus robur L., the common European oak. Pharmaceutical interest: The nuts of Fagus sylvatica L. (common beech) yield an oil. Castanea sativa Mill. (sweet or Spanish chestnut) yields timber and a bark used for tanning. The cupules and unripe acorns of Quercus aegelops (valonia) are used in tanning. Quercus suber afford the commonly used cork, in an industry worth £20 million to Portugal’s economy. Galls of Quercus infectoria, or Turkish galls, are an important source of tannic acid used in pharmacy. An extract of Quercus stenophylla has been marketed for the acceleration of the elimination of renal and urethral calculi. In the Asia-Pacific, a number of plants classified in the family Fagaceae are used owing to their astringent properties, to stop diarhea and bleeding, promote urination, counteract putrefaction and to soothe inflamed parts. Castanea crenata Sieb. & Zucc. [From Latin, castanea = chestnut and crenatus = with toothed edge] Physical description: It is a magnificent timber tree found in China, Korea and Japan. The bark is dark reddish

Common name: Japanese chestnut; Kuri (Japanese).

Subclass Hamamelidae

87

Uses: In China and Korea, the flowers are used to treat tuberculosis and scrofula, and a decoction of fresh leaves is used to resolve inflamed parts.

brown and the stems are glabrous. Leaves: simple, alternate and stipulate. The stipules are deciduous. The petiole is 9 mm–1.3 cm long.The blade is papery, 13.6 cm × 4 cm–11.5 cm × 3.5 cm, and lanceolate. The base of the blade is asymmetrical, somewhat cordate, and the apex ends in a 6 mm– 8 mm long tail. The margin is toothed, each tooth 2 mm long. The blade is Fig. 52. Castanea crenata Sieb. & Zucc. From: KLU Herbarium 8969. Geographical glabrous on the surface and covered localization: Chiba, 1957. Botanical Identificawith starry hairs underneath, showing tion: Benjamin C Stone, 9 Jan 1970. 14–17 pairs of secondary nerves. The midrib and secondary nerves are raised below and sunke above, and the midrib is somewhat hairy above.The flowers are tiny and packed in axillary 4 cm–7 cm long spikes (Fig. 52). Pharmaceutical interest: Anti-inflammatory properties: The anti-inflammatory property of Castanea crenata Sieb. & Zucc. is substanti- HO ated both in vitro and in vivo. Activity-guided fractionation of a water extract of leaves, based on the determination of inhibitory effect upon the release of hexosaminidase from RBL2H3 cells, led to the isolation of quercetin as the principle responsible for the inhibition of degranulation of mast cells (Lee E et al., 1999).

OH O

OH OH

OH

O Quercetin

References Lee E, et al. (1999) ArcHuman Immunodeficiency Viruses of Pharmaceutical Research 22(3): 320–323.

Warning: Caution must be taken as the toxic effects of this plant are unknown.

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Castanopsis cuspidata (Thunb.) Schottky [From Latin, castanopsis = chestnutlike and from cuspis = point]

Common names: Japanese tanbark oak; ita-shii (Japanese)

Physical description: It is a timber which grows wild in China and Japan. The wood is of commercial value. The stems are blackish, lenticelled, smooth and glabrous. The bark yields tannins. Leaves: simple, spiral and stipulate. The stipules are dioecious. The petiole is 1.5 cm–1 cm long, obscurely channeled above, and swollen at the base. The blade is lanceolate, glossy, leathery, and 8.9 cm×2.8 cm–9 cm×2.5 cm.The margin is laxly toothed and recurved. The base of the blade is acute, asymmetrical, and the apex is acuminate in a 1 cm–2 cm long tail. The blade shows 8–9 pairs of secondary nerves which are indistinct. The inflorescences are terminal spikes. The fruits are woody, globose. 1.4 cm long, velvety and scaly Fig. 53. Castanopsis cuspidata (Thunb.) Schottky. From: KLU Herbarium 21898. acorns (Fig. 53). Uses: In China, the bark of Castanopsis cuspidata (Thunb.) Schottky is used to treat ascite.

Ex. Herbario Kyotoensis. Flora of Japan. Botanical identification and field collectors: G. Murata & H. Tabata, 9 Aug 1974. Geographical localization: Ryuku (Pref. Okinawa). Isl. Iriomote: Shirahama. In evergreen forest near sea level.

Pharmaceutical interest: The pharmacological potential of Castanopsis cuspidata (Thunb.) Schottky would certainly be worth exploring as an expanding body of evidence, suggesting the genus castanopsis to abound with antimicrobial and cytotoxic principles. Antimicrobial properties: Galloylshikimates and galloylquinates isolated from Castanopsis hystrix inhibit the enzymatic activity of Human Immunodeficiency Virus type-1 reverse-transcriptase (Chang CW et al., 1995). The seeds of Castanopsis chinensis elaborate a 30 KDa protein (20 mg/10 Kg of seeds) which alleviates Botrytis cinerea, Fusarium oxysporum, Mycosphaerella arachidicola, and Physalospora piricola, with an IC50 value of 0.5 mM against Fusarium oxysporum. This protein exhibits also a potent inhibitory activity on Human Immunodeficiency Virus type-1 reverse-transcriptase with IC50 value of 1.6 µM

Subclass Hamamelidae

89

(Chu KT et al., 2003). A root extract of Castanopsis cf evansii immobilizes brine shrimps at 100 mg/mL (Horgen FD et al., 2001). A methanol extract of the stem and the root bark of Castanopsis acuminatissima shows a broad spectrum of antimicrobial activity (Khan MR et al., 2001). References Chang CW, et al. (1995) Antiviral Res 27(4): 367–374. Chu KT, et al. (2003) Biochem Biophys Res Commun 301(2): 364–370. Khan MR, et al. (2001) Fitoterapia 72(2): 174–176. Horgen FD, et al. (2001) Phytomedicine 8(1): 71–81.

Warning: Caution must be taken as the toxic effects of this plant are unknown. Lithocarpus elegans (Bl.) Hatus. ex Soepadmo [From Greek, Lithos = stone, karpos = fruit and from French, elegant = handsome] Synonymy: Lithocarpus spicata Rehd. & Wils. Common names: Mempening bangkas (Malay).

Physical description: It is a timber which grows to a height of 20 m. The plant grows in the secondary or degraded rainforest in the geographical areas spanning India, Vietnam and Indonesia. The bark is greenish-white and the inner bark light yellowish-brown. The sapwood is white. The wood is very hard and heavy. The stems are brown, lenti- Fig. 54. Lithocarpus elegans (Bl.) Hatus. ex celled and smooth. Leaves: simple, Soepadmo. From: KLU Herbarium 006267. spiral, and stipulate. The stipules are Flora of Malaya. Field collector: MED Poore, 5 triangular to linear and deciduous. The Oct 1963. Geographical localization: Hill forest, edge of the road just west of the Gap, Mile 56. petiole is 8 mm–1 cm long and some- Botanical Identification: E Soepadmo IV.1968. what swollen at the base. The blade is 9.8 cm × 4.7 cm–12 cm × 4.5 cm, and leathery. Both the apex and the base of the blade are acute. The margin is entire and wavy. The blade shows 10–12 pairs of secondary nerves. The inflorescences are stout, woody, and 16.5 cm–11 cm × 5 mm terminal spikes. The fruits are leathery, glossy and smooth 1.3 cm × 1.1 cm acorns. The cupules are rugose (Fig. 54).

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Pharmaceutical interest: The pharmaUses: In China, the fruits and the cological potential of this plant remains leaves of Lithocarpus elegans unexplored. However, note that the medic(Bl.) Hatus. ex Soepadmo are inal property mentioned above is most used to check menorrhagia. probably attributed to tannins which are astringent, precipitate proteins and therefore styptic. These tannins are probably responsible for the toxicity of the root and stem bark of Lithocarpus sp. 1 against Plasmodium falciparum cultured in vitro at a dose of 10 µg/mL (Horgen FD et al., 2001). A methanol extract of the leaves, stem and root barks of Lithocarpus celebicus inhibits the growth of a broad spectrum of bacteria (Khan MR et al., 2001). Are tannins involved here again?. It will be interesting to learn whether more intensive future research on Lithocarpus elegans (Bl.) Hatus. ex Soepadmo will disclose any molecules of therapeutic interest. References Horgen FD, et al. (2001) Phytomedicine 8(1): 71–81. Khan MR, et al. (2001) Fitoterapia 72(6): 703–705.

Warning: Caution must be taken as the toxic effects of this plant are unknown. Quercus acutissima Carruthers [From Latin, quercus = the oak and acutus = sharpen] Physical description: Quercus acutissima Carruthers is a tree native to China, Japan and Korea. It is widespread in temperate Asia and is even found in the US. The stems are greyish, lenticelled, and hairy. Leaves: simple, spiral and stipulate. Common name: Sawtooth oak; kunugi (Japanese). Uses: In China, the acorns are astringent and used to treat diarrhea, flux, prolapse of the rectum, to promote resorption of tuberculous nodules and to check menorrhagia. In Korea, the acorns are used to stop diarrhea. The pharmacological properties of this plant are yet unveiled. Are tannins involved here?

Fig. 55. Quercus acutissima Carruther. From: KLU 043859. The Forest Herbarium (BKF), Royal Forest Department. Flora of Thailand. Field collector & botanical identification: D Bunpheng, 29 Sep 1949. Geographical localization Thailand, Northeast: Loei, Phu Krading.

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The stipules are deciduous. The petiole is long and flat above. The surface of the blade is lanceolate, glabrous, except the midrib, 16 cm × 5 cm–4 cm × 11 cm and coriaceous. The base of the blade is asymmetrical and the apex is acute. The margin is conspicuously toothed, and each tooth is 3 mm long. The blade shows 3–6 pairs of secondary nerves with tufts of hairs near the margin. The inflorescences are spikes. The fruits are glossy acorns with fluffy involucres of 2.5 cm diameter (Fig. 55).

III. Subclass CARYOPHYLLIDAE Takhtajan 1966 The Caryophyllidae consists of 3 orders, 14 families and about 11 000 species of herbaceous plants. It developed some 70 million years ago from the subclass Magnoliidae, through the order Ranunculales and is considered quite a recent development, compared with the Magnoliidae, Hamamelidae, Dilleniidae and Rosidae (Appendix I). The gynecium of Caryophyllidae comprises of a finite number of carpels united to form an inferior ovary, where ovules are attached to free central or basal placentas. In the andrecium, the stamens are inserted in a centrifugal sequence. Common chemical weapons used by Caryophyllidae are triterpenoid saponins.Triterpenoids saponin are surface-acting agents which dissolve the cytoplasmic membrane of Eukaryotic cells and impede nutrition. Note that triterpenes resembling our own steroidal hormones have therefore the tendency to exert among other things anti-inflammatory and diuretic activities. Other interesting principles of Caryophyllidae are alkaloids, lectins, peptides and oligo- or polysaccharides. The triterpenoid saponins of Caryophyllales are historically of pharmaceutical value.

A. Order CARYOPHYLLALES Bentham & Hooker 1862 Nine-tenths of the species in Caryophyllidae belong to the single order Caryophyllales which consists of 12 families and about 10 000 species of herbs. An interesting feature of this order and particularly of Phytolacca americana L. (pokeweed) is the production of ribosome-inactivating proteins which have potent anti-HIV activities. Note that most Caryophyllales have evolved from the family Phytolaccaceae and are therefore disposed to produce such proteins. The very few alkaloids present in this order would be worth investigating.

1. Family AIZOACEAE Rudolphi 1830 nom. conserv., the Fig — marigold Family Physical description: The family Aizoaceae consists of about 2500 species and about 12 genera of succulent herbs, sometimes cactus-like, or less often shrubs or subshrubs known to abound with triterpenoid saponins and oxalic acid. The leaves are opposite, alternate, and without stipules. The

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inflorescences are solitary or cymose. The flowers are perfect, and comprise of 3–8 sepals, and numerous petals in 1–6 whorls. The andrecium consists of 1– many stamens originating in a centrifugal sequence. The gynecium consists of 2–5 carpels united in a compound ovary. The fruits are loculicidal capsules.

NH2 HO N H Serotonine

OCH3 Pharmaceutical interest: Many species of Aizoaceae are decorative and are cultivated as such. Some, H3CO notably from the genus Mesembryanthemum, have become naturalized in many parts of Europe. Examples of medicinal Aizoaceae are Galenia africana and Sceletium tortuosum, which are used in African indigenous medicine as a counter-irritant in the treatment of N O toothache. The counter-irritant property is due to crysCH3 tals of oxalic acid which penetrate mucosa and skin. Mesembrine Oxalic acid is toxic. In the body, it combines with calcium ions to form calcium oxalate which precipitates in the kidneys. Mesembryanthemum crystalinum (ice plant) was considered a sure treatment for venereal diseases by the early cowboys of western North America. Kanna or Sceletium expansum and Sceletium tortuosum, have been used by South African shamans from prehistoric times to “enhance animal spirits, sparkle the eyes, and to stimulate gaiety”. The active constituent of kanna is a serotonine-like alkaloid called mesembrine which is a potent serotonine uptake inhibitor. Hence, it has some potential for the treatment of anxiety and depression, but careful clinical trials must be performed. In the Asia-Pacific, Tetragonia tetragonoides (Pallas) O. Ktze. and Trianthema portulacastrum L. are of medicinal value.

Tetragonia tetragonioides (Pallas) O. Ktze. [From Greek, tettares = four and gonos ˆ = angled] Physical description: It is a herb Synonymy: Tetragonia expansa Murr. native to the Southern Hemisphere. It grows by the roads, along seashores Common names: New Zealand spinach, New England spinach, and on the sea cliffs of the Pacific warrigal cabbage. region, South America to Japan and Southeast China (including Norfolk and Lord Howe Islands), New Zealand, Australia, Tasmania, the Kermadec Islands, New Caledonia, Hawaii, and other Pacific Islands. It is widely naturalized in the temperate and subtropical parts of the world as an escape from cultivation. It is commonly found in California on sand dunes, bluffs, and the margins

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Uses: Most of the aborigine peoples of the southern part of Australia have been using Tetragonia tetragonioides (Pallas) O. Ktze. as a vegetable since the prehistoric times. They introduced it to the European explorers of the 17th century and it became the first Australian food plant to be cultivated overseas, the seeds being taken to Kew Gardens by Banks in 1771. Seeds were later distributed from Kew to Europe and North America. In Japan, a decoction of the dried plant is drunk to treat carcinoma ventriculi. The fresh plant is used to treat scurvy. The whole plant is used to heal stomach ulcers. Fig. 56. Tetragonia tetragonoides (Pallas) O.

of coastal wetlands below 100 m. The Ktze. stems are succulent and glabrous. Leaves: simple, without stipules, alternate and 6 cm × 2.5 cm–9 cm × 5 cm. The blade is deltoid and very thin, and the margin is slightly wavy. The apex of the blade is acute to round and the base is tapering towards the stem. The midrib is flat above and below the blade which shows about 4 pairs of discrete secondary nerves. The fruits are solitary, axillary, woody, 8 mm × 6 mm, and 4-angled (Fig. 56). Note that the plant is often misspelt as Tetragonoides. Pharmaceutical interest: The antiulcer properties of Tetragonia tetragonioides (Pallas) O. Ktze. are attributed to cerebrosides and sterylglucosides (Okuyama E et al., 1983, 1983a). A number of polysaccharides were isolated from this plant and their anti-inflammatory effects on carrageenan-induced edema and adjuvant arthritis were tested. Note that this plant is rich in vitamin C. References Okuyama E, et al. (1983) Chem Pharm Bull 31(7): 2209–2219. Okuyama E, et al. (1983a) Yakugaku Zasshi 103(1): 43–48.

Warning: Caution must be taken since the toxic effects of this plant are unknown. Trianthema portulacastrum L. [From Greek, treis = three and anthemon = flower and from Latin, portulacastrum = portulaca-like]

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Common name: Horse-purslane.

Physical description: It is a tropical herb which grows to a height of 1 m. The stems are glabrous and fleshy. Leaves: simple, opposite, without stipules and 3 cm–7 cm× 1.5 cm–4.5 cm. The petiole is 8 mm–2 cm long, sheathing at the base and channeled. The blade is 2 cm–4.4 cm×1.5 cm–4.5 cm, orbicular and succulent. The apex is round or notched. The base is tapered and asymmetrical. The midrib is showy and flattened on both sides of the blade which shows 4– 5 pairs of secondary nerves. The tertiary nerves form characteristic spiral patterns (Fig. 57).

Fig. 57. Trianthema portulacastrum L.

OH Trianthenol 1

Pharmaceutical interest: Hepatoprotective properties: Daily oral Uses: The fresh or dried plant of the feeding with an ethanolic extract of white variety of Trianthema portulathis plant (150 mg/Kg) protects hepcastrum L. (Trianthema, Indian Pharatocytes against carbon tetrachlomacopoeia, 1967) is used in India to ride poisoning (Sarkar A. et al., promote urination, in the form of a 1999). A chloroformic extract of Triliquid extract (2 in 1, dose 2 mL to anthema portulacastrum L. protects 8 mL). A decoction of the roots causes mild contraction of the uterus, but male Sprague-Dawley rats against Lin large doses it is abortive. In the diethylnitroso-amine-induced and phPhilippines, a decoction of the roots is enobarbital-promoted hepatocarcinodrunk to promote menses and to abort genesis (Battacharya S et al., 1999). a pregnancy. These effects could be mediated by trianthenol 1, a carotenoid which was first isolated as antifungal principle (Nawar HR et al., 2001). Other properties: This plant contains an alkaloid with similar properties to punarvanine from Boerhaavia diffusa (Family Nyctaginaceae; Basu et al., 1947). The diuretic, uterotonic and abortive properties of this plant have not yet been substantiated experimentally.

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References Basu, et al. (1947) Quart J Pharm 20, 39. Bhattacharya S, et al. (1999) Neoplasma 46(2): 105–111. Nawaz HR, et al. (2001) Phytochem 56(1): 99–102. Sarkar A, et al. (1999) Cell Biol Int 23(10): 703–708.

Warning: Caution must be taken as the toxic effects of this plant are unknown.

2. Family CACTACEAE A. L. de Jussieu 1789 nom. conserv., the Cactus Family Physical description: The family Cactaceae consists of 100 genera and about 2000 species of xerophytic plants native to South America which are thought to have originated from the family Phytolaccaceae. Cactaceae produce triterpenoid saponins, mucilages, simple tetrahydroisoquinoline and phenethylamine alkaloids. The stems are succulent with scarcely developed leaves. The flowers are solitary, hermaphrodite, large, and showy, and comprise of several sepals and stamens initiated in a centrifugal sequence. The gynecium consists of 3–several carpels united in an inferior and more or less partitioned ovary which encloses 3–several ovules attached to parietal placentas. The fruits are berries. Pharmaceutical interest: Cactaceae of the genera Carnegia, Coryphanta, Marginatocereus and Lophophora are known to produce epinephrine-like hallucinogen alkaloids. These are phenethylamine alkaloids derived from phenylalanine and tyrosine. Lophophora williamsii (Echinocactus williamsii (Lem. OCH3 OH ex Salm-Dick) Coult.) or peyote, pey- H3CO HO OCH3 otl, anhalonium or mescal button, has been used by American shamans to cause hallucination. Peyote contains mescaline, the clinical properties of HO which are similar to those of lysergic NH2 NH2 acid diethylamide (Fig. 58). A few introMescaline Noradrenaline duced Cactaceae species are used for medicinal purposes in Asia-Pacific, Fig. 58. Examples of neuroactive natural prodtwo of these are Opuntia dillenii ucts characterized from the family Cactaceae. (Ker — Gawl.) Haworth and Pereskia Note the similitude of chemical structure between mescaline and noradrenaline. bleo DC.

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Opuntia dillenii (Ker — Gawl.) Haworth [From Greek, opunte = a city of ancient Greece and Johann Jacob Dillenius (1648–1747), a German botanist and Professor of Botany at Oxford] Synonymy: Cactus indicus Roxb. Common names: Prickly pear, slipper thorn; kalazaw (Burmese); raquette, figue de Barbarie (French); palmatoria d’inferno (Portuguese); guda (Sanskrit); kalli (Tamil).

Physical description: It is a shrubby cactus which grows to a height of 2 m. It is native to Central America. The plant is ornamental and cultivated as such throughout the trop- Fig. 58. (a) Opuntia dillenii (Ker–Gawl.) Haworth. ics. The stems are 30 cm–40 cm × 15 cm–20 cm, broadly obovate, undulate, succulent, spiny and bluish. The leaves are 3.8 mm long, pale green, and conical. The areoles are large, and bear 4–6, 2.5 cm–3.8 cm prickles each. There are several 1.3 cm long yellowish glochidia. The flowers are 7.5 cm long, yellow, and tinged with orange. The perianth is rotate and reddish. The stamens are numerous and longer than the corolla. The style is stout, and there are 5–8 erect stigmas. The fruits consist of pyriform berries, which are truncate, depressed at the apex, deep reddishpurple when ripe and bearing tiny tufts of glochidia [Fig. 58(a)]. Pharmaceutical interest:

Uses: In China, the stems of Opun-

tia dillenii (Ker — Gawl.) Haworth are Anti-inflammatory and analgesic propmacerated in a little water or baked, erties: A lyophilized aqueous extract and applied externally to heal deepof fruits protects rats against the seated abscesses on the sole of the paw edema formation induced by carfeet, and to soothe inflamed parts. In rageenans and the pain caused by India, Opuntia dillenii (Ker — Gawl.) chemicals (writhing test) and heat Haworth is used to relieve the bow(hot plate test), with doses rangels of costiveness, promote digesing from 100 mg/Kg–400 mg/Kg, i.p. tion, stop flatulence, treat fever and to and 50 mg/Kg and 100 mg/Kg respecresolve inflammation. tively (Loro JF et al., 1999). Ethanolic extracts of fruits and stems of Opuntia ficus-indica display interesting analgesic and anti-inflammatory properties experimentally (Park EH et al., 1998). Oral administration of these extracts suppresses in rats acetic acid-induced writhing syndrome and carrageenan-induced paw-oedema. These extracts inhibit the migration of leukocytes, the release of β-glucuronidase by rat neutrophils and

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protect the gastric mucosa. One might think that the anti-inflammatory and analgesic properties of Opuntia dillenii (Ker–Gawl) Haworth and Opuntia ficusindica could be both mediated by flavonoids such as opuntioside I, 4-ethoxyl6-hydroxymethyl-α-pyrone, and kaempferol 7-O-β-D-glucopyranosyl-(1 → 4)β-D-glucopyranoside (Qiu Y et al., 2002) or mucilages. Dietetic properties: Of particular interest in Opuntia species are neutral mucilages called glucomannans which impede the metabolism of sugars and lipids. This mucilages are possibly involved in the gastroregulator properties of Opuntia dillenii (Ker–Gawl) Haworth. The mucilages extracted from Opuntia species decrease the plasma concentration of low density lipoproteins in guinea-pigs fed with a hypercholesterolaemic diet (Fernandez ML et al., 1992). A purified extract of Opuntia fuliginosa reduces to normal levels blood glucose and glycated hemoglobin values in streptozocin-induced diabetic rats (TrejoGonzalez A et al., 1996). Opuntia streptacantha decreases significantly the hyperglycaemic peaks in healthy rabbits submitted moderately to subcutaneous glucose tolerance tests (Roman-Ramos R et al., 1995). Commercial capsules of dried Opuntia ficus or nopal given to diabetic subjects fail to show significant hypoglycaemic effects (Frati-Munani AC et al., 1992). In regard to the sugar metabolism, a number of experiments conducted in normal and diabetic subjects tend to demonstrate that the addition of neutral mucilages such as guar of Cyamopsis tetragonolobus (L.) Taub. (Fabaceae, p.) to the food ration decreases both blood sugar and postprandial insulinaemia. This effect would principally be on account of the high viscosity of these mucilages, which delay gastric emptying and reduce the rate of absorption of sugars in the intestine. In the case of lipid metabolism, the daily intake of guar, for example, decreases serum cholesterol and low density lipoproteins without notably affecting other lipoproteins and without decreasing blood triglycerides. Glucomannans of Amorphophallus konjac Koch. (Araceae, p.) have become available in the market (capsules, jelly) as adjunct in low-calorie diets and to control cholesterolaemia. Another example of a plant containing neutral mucilage is Trigonella foenum graceum L. (Fabaceae), the seeds of which are known for their antidiabetic, blood cholesterol-lowering, and blood lipid-lowering properties. Antiviral properties: An extract of Opuntia streptacantha inhibits the replication of the Herpes Simplex Virus type 2, Equine Herpes Virus, Pseudorabies Virus, Influenza Virus, Respiratory Syncytial Virus and Human Immunodeficiency Virus (Ahmad A et al., 1996). References Ahmad A, et al. (1996) Antiviral Res 30(2–3): 75–85. Fernandez ML, et al. (1992) J Nutr 122(12): 2330–2340. Frati-Munani AC, et al. (1992) J Med Mex 128(4): 431–432.

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Loro JF, et al. (1999) J Ethnopharmacol 1;67(2): 213–218. Park EH, et al. (1998) Arch Pharm Res 21(1): 30–34. Qiu Y, et al. (2002) Chem Pharm Bull 50(11): 1507–1510. Roman-Ramos R, et al. (1995) J Ethnopharmacol 48(1): 25–32. Trejo-Gonzalez A, et al. (1996) J Ethnopharmacol 55(1): 27–33.

Warning: Caution must be taken as the toxic effects of this plant are unknown. Pereskia bleo DC [After the French astronomer Nicolas Claude Fabri de Peiresc (1580– 1637) and from a local South American, bleo = Pereskia bleo DC] Physical description: It is a spiny shrub which grows to a height of 2– 8 m. It is native to South America and cultivated in several tropical countries for decorative and medicinal purposes. Leaves: simple, spiral, glossy and succulent. The petiole is 3 cm long. The blade is lanceolate and 6 cm–20 cm × 2 cm–7 cm. The areoles produce 0– 5, 5 mm–1 cm long spines on young stems, and up to 40, 2 cm long spines for older stems. The flowers are 4 cm–6 cm, red or orange, terminal, grouped by 2–4 and showy. The fruits are 4 cm–5 cm in diameter, fleshy and glossy conical berries containing 6 mm–8 mm diameter seeds (Fig. 59). Common name: Wax rose. Uses: In Malaysia, Pereskia bleo is used internally to treat cancer.

Pharmaceutical interest: There is an expanding body of evidence to suggest that Perecksia species are of chemotherapeutic value. A methanolic extract of Pereskia bleo DC induce apoptosis in breast carcinoma, T47-D cell line (Tan ML et al., 2005) and a

Fig. 59. Pereskia bleo DC.

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methanol extract of Pereskia corrugata inhibits the growth of T-47D human breast carcinoma cell line cultured in vitro with an EC50 value below 2 µg/mL and induces apoptosis, via activation of caspase-3 and c-myc pathway (Lan MT et al., 2001). What are the principles involved here? Polysaccharides, flavonoid glycosides? Reference Tan ML, et al. (2005) J Ethnopharmacol 96(1–2): 287–294.

3. Family CHENOPODIACEAE Ventenat 1799 nom. conserv., the Goosefoot Family Physical description: The family Chenopodiaceae consists of about 100 genera and 1500 species of annual or perennial, halophyte, and succulent herbs which are ubiquitously distributed and especially abundant in dry regions and coastal areas. Chenopodiaceae and Amaranthaceae have evolved side by side from the Phytolaccaceae and form a special group of small-flowered Caryophyllales. Chenopodiaceae accumulate triterpenoid saponins, oxalic acid and quite often free nitrate. The leaves in this family are thick, waxy, alternate or rarely opposite, simple and without stipules and often 3-lobed like a “foot of a goose”, hence the name of the family which comes from the Greek words cheen ´ for goose and pous for foot. Flowers of Chenopodiaceae are very small, unisexual or hermaphrodite, and actinomorphic.The perianth comprises of 3–5 imbricate sepals often accrescent in fruits. The andrecium consists of 3–5 stamens which are free and facing the sepals. The gynecium consists of 2–5 carpels united to form a compound and unilocular superior ovary which encloses a single ovule. The fruits are very small nuts. Pharmaceutical interest: Classical examples of Chenopodiaceae are Spinacia oleracea L. (spinach), Beta vulgaris L. (beetroot) and Chenopodium ambrosioides var. anthelminticum.The dried fruits of O O Chenopodium ambrosioides var. anthelminticum (Chenopodium, British Pharmaceutical Codex, 1949) and the oil obtained by steam distillation of fresh flowering and fruiting parts of Chenopodium ambrosioides var. anthelminticum (Chenopodium Oil, British Phar- Ascaridole maceutical Codex, 1959) containing not less than 65% w/w of the endoperoxidic monoterpene ascaridole have been used to expel roundworms. An interesting feature of Chenopodiaceae is their ability to produce a few indole alkaloids, the therapeutic potential of which is open for pharmacological exploration. One such alkaloid is dipterin from Arthrophytum leptocladum and Girgensohnia dipter which is well known for its antihypotensive property.

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Beta vulgaris L., Chenopodium album L., Chenopodium ambrosoides L. var. anthelminticum and Kochia scoparia (L.) Schrad. are used for medicinal purposes in the Asia-Pacific. Note that most medicinal Chenopodiaceae owe their properties to saponins which are antiseptic and anti-inflammatory.

Chenopodium album L. [From Greek, cheen ´ = goose and pous = foot and from Latin, albus = white] Physical description: It is an invasive weed found in temperate countries, which grows to a height of 50 cm. The stems are glabrous, greenish and somewhat succulent. Leaves: simple, alternate and without stipules. The petiole is 1.5 cm–5 mm long, grooved and covered with microscopic cupshaped scales. The blade is thick, 2.5 cm × 3.2 cm–1.8 cm × 7 mm, triangular, incised, and covered with microscopic cup-shaped scales.The base of the blade is acuminate, the midrib and secondary nerves are flat above and raised below, and the blade shows 3– 5 pairs of secondary nerves. The inflorescences are axillary or terminal 2 cm long spikes. The flowers are 2 mm in diameter and comprise of 5 sepals, 5 stamens and a bifid style. The seeds are very small and black (Fig. 60).

Common names: Lamb’s quarter, pigweed, all-good, fat hen, muck-weed; chenopode sauvage (French); farinaccio (Italian); ceniglo blanco (Spanish); vastu (Sanskrit).

Pharmaceutical interest: Chenopodium album L. contains saponins, Uses: In Burma, a paste made from the root is used to stop diarrhea in children. In China, the seeds are eaten to expel intestinal worms and the juice of the fresh plant is applied externally to resolve sunburn. In Vietnam, the plant is used to treat putrefaction of the genitals.

Fig. 60. Chenopodium album L. From: KLU Herbarium 15209. Geographical localization: Moss Side — Manchester (arable land, common) United Kingdom. Field collector & botanical identification: Wai Lu Lee, 2 Aug. 1971.

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ascorbic acid (Guil JL et al., 1997; Lavaud C et al., 2000) and N-trans-feruloy l-4-O-methyldopamine which shows attracting activity toward the spores of Aphanomyces cochlioides, a fungus pathogenic for Chenopodium species (Takeshi H et al., 1993). An ethanol extract of the fruits of Chenopodium album L. given orally at doses of 100 mg/Kg–400 mg/Kg to mice dose-dependently inhibits itchiness induced by the subcutaneous injection of serotonine (Dai Y et al., 2002). OH OCH3

O N H HO

OCH3 N - trans - feruloyl - 4 - O - methyldopamine

References Dai Y, et al. (2002) J Ethnopharmacol 81(2): 245–50. Guil JL, et al. (1997) Plant Food Hum Nutr 51(2): 99–107. Lavaud C, et al. (2000) Fitoter 71(3): 338–340. Ozmen O, et al. (2003) Vet Hum Toxicol 45(2): 83–84. Takeshi H, et al. (1993) Phytochem 33(4): 807–808.

Warning: Chenopodiaceae accumulates toxic levels of nitrates when growing in fertilized lands. Cattle show ataxia, bluish-brown mucous membranes, rapid and difficult breathing, increased heart rates, tremors and coma after grazing hay containing 2500 ppm nitrate-nitrogen and 11 ppm nitrite nitrogen (Ozmen O et al., 2003). Kochia scoparia (L.) Schrader [After Wilhelm Daniel Josef Koch, (1771–1849), German doctor and professor of botany and from Latin, scoparius = broom–like] Physical description: It is a very Common names: Summer cypress, dense, cypress-like bush which grows fire weed; fireball, Mexican firewood, in the geographical zones spanning ti fu (Chinese). Central Asia and Japan.The stems are yellowish, glabrous, terete and ribbed. Leaves: simple, spiral, sessile, and without stipules. The blade is linear, glabrous, and small. The margin is entire.

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The blade shows a single pair of secondary nerves visible from below only. The flowers are small and yellow (Fig. 61). Uses: In China and Japan, the seeds of Kochia scoparia (L.) Schrader are eaten to promote urination, to invigorate health, and to treat scurvy, impotency, gonorrhea and kidney problems. A decoction of Kochia scoparia (L.) Schrader is drunk to counteract putrefaction and to promote urination. The aerial parts are used to treat digestive disorders.

Pharmaceutical interest: Anti-inflammatory and analgesic properties: The dried fruits of Kochia scoparia (L.) Schrader inhibit humoral Fig. 61. Kochia scoparia (L.) Schrader. immunity in experimental models of From: KLU Herbarium 22097. Field Collector: G Murata. Geographical localization: Honshu, type I-IV allergy on account of an Pref. Hyogo: Oshio, Himeji-shi, seaside, Japan, oleanolic saponin, momordicin Ic, 31 Oct 1971. which is also able to inhibit glucose and ethanol absorption in rats (Matsuda H et al., 1997; Yoshikama M et al., 1997). An extract of seeds displays peripheral antinociceptive effects (Matsuda H et al., 1997a) and kochianosides I-IV are antiprurinogen (Yoshikama M et al., 1997a). References Dickie CW, et al. (1979) J Am Vet Med Assoc 175(5): 463–465. Matsuda H, et al. (1997) Biol Pharm Bull 20(11): 1165–1170. Matsuda H, et al. (1997a) Biol Pharm Bull 20(10): 1086–1091. Yoshikama M, et al. (1997) Chem Pharm Bull (Tokyo) 45(8): 1300–1305. Yoshikama M, et al. (1997a) Chem Pharm Bull 45(6): 1052–1055.

Warning: Kochia scoparia (L.) Schrader like Chenopodium album L. has the tendency to accumulate high levels of nitrates when grown in fertilized lands. This results in pulmonary edema, hepatic necrosis, and kidney, epidermal and cerebral necrosis, as well as lacrimation, depression, anorexia, nystagmus, recumbency, episthotonos and death in cattle (Dickie CW et al., 1979).

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4. Family AMARANTHACEAE A. L. de Jussieu 1789 nom. conserv., the Amaranth Family Physical description: The family Amaranthaceae consists of about 70 genera and 800 species of tropical herbs containing triterpenoid saponins. Leaves in Amaranthaceae are simple, without stipules, alternate or opposite, serrate or entire. The flowers are very small, without petals, and packed in spikes, racemes or panicles. The perianth consists of a few free and very thin sepals facing a few stamens, the filaments of which are united at the base in a cup or tube. The gynecium consists of 2–3 carpels united to form a 1-celled and superior ovary, containing 1–2 ovules attached to a basal placenta. The stigma is capitate, or bifid or trifid. The fruits are very small utricles, alkenes or capsules. Pharmaceutical interest: Common examples of Amaranthaceae are Celosia cristata L. and Amaranthus blitum L. which are ornamental and palatable respectively. In the Asia-Pacific, Amaranthaceae are not only important for providing vegetables but also for providing about 20 species of medicinal plants used to resolve inflammation, stop dysentery, counteract putrefaction, promote urination, facilitate parturition and to check bleeding. Being occulted often, the family Amaranthaceae, however, offers an interesting field of pharmacological research and therapeutic developments. Of particular interest are oligosaccharides of possible chemotherapeutic value. Achyranthes aspera L. [From Greek, achyr = barb, anthe = flower and from Latin, asper = rough] Physical description: It is a tropiSynonymy: Pupalia genulata, cal, upright, hairy, and branched herb Achyranthes indica. which grows up to a height of 1.8 m Common names: Prickly chaff in villages, orchards and sandy dunes. flower; herbe d’Inde (French); ara Leaves: simple, without stipules and songsang, nyarang (Malay); 1.25 cm–4 cm × 1.5 cm–7.5 cm. The kivalamon (Burmese); nieou si blade is more or less hairy and broadly (Chinese); adhoghanta (among 30 elliptic. The petiole is 5 mm–1.25 cm others Sanskrit names); unga, long. The flowers are packed in 7 cm chichira, atkumah, latjira (Indian). long, reddish-white, hairy, and terminal spikes. The flowers consist of 5 narrow, pointed and 5 mm long green sepals. The andrecium consists of 5 stamens which are joined at the base around the

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ovary into a fringed cup. The fruits are cylindrical utricles containing black and glossy ellipsoid seeds (Fig. 62). Pharmaceutical interest: Antimicrobial properties: In regard to the antiseptic properties mentioned above, a number of experiments conducted in vitro and in vivo demonstrate that Achyranthes aspera L. is antimicrobial on account of at least 3 groups of probably synergistic series secondary metabolites: terpenes, alkaloids and phenolic compounds. The essential oil extracted from the shoots inhibits moderately the proliferation of Aspergillus carneus (minimum inhibiting concentration = 3000 ppm; Misra TN et al., 1992). The seeds of Achyranthes aspera L contain a number of oleanolic triterpenoid saponins which inhibit the proliferation of Bacillus subtilis, Escherichia coli and Salmonella thyphimurium (Sushil K et al., 1997). Aporphinoid alkaloids from the stems inhibit the proliferation of Bacillus subtilis, Pseudomonas aeruginosa, Staphylococcus aureus, and Shigella dysenteriae (Rahman RH et al., 1996). A decoction of Achyranthes aspera L. is effective (30 mL twice daily) in the treatment of subacute and mild type reactions in leprous patients (Ojha D et al., 1966). Steroidal properties: One might set up the hypothesis that the antiinflammatory and diuretic properties of Achyranthes aspera L. involve a corticosteroid-based mechanism of action. In physiological conditions, corticosteroids are transferred to their cell

Fig. 62. Achyranthes aspera L.

Uses: In Indonesia, a paste of Achyranthes aspera L. mixed with the bark of Alyxia stellata (Roem.) et Schult. and the fruits of Foeniculum vulgare Gaertn. is applied to the body to treat convulsion. A decoction of this mixture is drunk to stop dysentery. Achyranthes aspera L is used to promote urination and it is an astringent remedy. In Malaysia, Achyranthes aspera L. is used to resolve inflamed parts, lower blood pressure and to counteract infection of the urinary tract. In the Solomon Islands, a paste made from the powdered leaves is applied to boils and the roots are used to treat swollen legs. In Vietnam, roasted leaves are used externally to heal burns and an infusion of the roots is ingested to mitigate colic. In India, a decoction of Achyranthes aspera L. (1 in 15; dose 30 mL to 60 mL) is drunk to promote urination and the seeds are eaten to treat piles. The white variety of Achyranthes aspera L. is said to be more efficient against piles, ascite and dysentery whereas the red variety is preferred for ulcers.

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targets, in plasma, bound to a corticosteroid-binding globulin. Unbound or free corticosteroids enter the target-cells and bind to a cytoplasmic corticosteroid receptor. The dimer corticosteroid-receptor enters then the nucleus and binds to a DNA binding receptor and stimulates therefore the synthesis of specific proteins with physiological properties. A number of plant triterpenoids and steroids share with human steroid a cyclopentanoperhydrophenanthrene skeleton and are thereby able to interfere with the manifold physiological activities of steroidal hormones, hence exhibiting anti-inflammatory, diuretic, hypoglycaemic, estrogen antagonist, and abortifacient properties (Pakrashi A et al., 1977; Wadhwa V et al., 1986; Figs. 63–64). Normal and alloxan-induced diabetic rabbits fed with Achyranthes aspera L. or aqueous and methanolic extracts, develop a dose-dependent hypoglycaemia at doses of 2 g/Kg, 3 g/Kg, and 4 g/Kg (Akhtar MS et al., 1991).The anti-inflammatory property of Achyranthes aspera L. could be on account of an inhibition of phospholipase A2 activity through lipocortine, the synthesis of which is physiologically monitored by corticosteroids. The diuretic property of Achyranthes aspera L. may be attributed to an inhibition of the corticosteroid-induced synthesis of Na+ -pumps of the distal nephron and collecting duct-cells. Finally, the hypoglycemic property of Achyranthes aspera L may be on account of an inhibition of the liver corticoidinduced glucose synthesis, and in peripheral tissues, corticosteroid-induced decrease of glucose intake.

O O OH

OH

O

HO Stigmasterol

Cortisone

COOH

HO

Oleanolic acid

Fig. 63. Note the similitude of chemical structure of plant steroids (stigmasterol), cortisone and plant triterpenes (oleanolic acid).

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Fig. 64. Oleanolic acid (T) binds to corticosteroid-binding globulin (CBG), corticosteroid receptor (CR) or DNA-binding domain (DBD). Anti-inflammatory effect: stimulation of the synthesis of lipocortine (L) and therefore inhibition of phospholipase A2 (P).

Antitumor properties: A methanolic extract of Achyranthes aspera L. inhibits the early expression by Raji cells of Epstein-Barr Virus (EBV) antigen induced by 12-O-tetradecanoylphorbol-13-acetate (TPA) and displays an anticarcinogenic property in vivo (Chakraborty A et al., 2002). What is the active principle involved here? References Akhtar MS, et al. (1991) J Ethnopharmacol 31(1): 49–57. Chakraborty A, et al. (2002) Cancer Lett 177(1): 1–5. Misra TN, et al. (1992) Phytochem 31(5): 1811–1812. Ojha D, et al. (1966) Lepr Rev 37, 115. Pakrashi A, et al. (1977) Ind J Exp Biol 15(10): 856–858. Rahman MH, et al. (1996) Fitoter 67(1): 92–93. Sushil K, et al. (1997) Int J Pharmacog 35(3): 179–184. Wadhwa V, et al. (1986) Planta Med (3): 231–233.

Warning: Caution must be taken as the toxic effects of this plant are unknown.

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Achyranthes bidentata Bl. [From Greek, achyr = barb, anthe = flower and from Latin, bi = two and dentatus = with teeth] Physical description: It is a slender and Synonymy: Achyranthes mollicula. perennial herb which grows to a height Common names: Ox knee; niu xi of 1 m. It is found in moist and shady (Chinese). grounds in India, Southeast Asia, China and Japan. The stems are quadrangular and pubescent, and develop regular large knee-shaped nodes, hence the common name of the plant. Leaves: simple, without stipules, opposite, 5 cm–12 cm × 3 cm–5 cm, acuminate, and tomentose on both surfaces. The inflorescences are terminal or axillary of 2 cm–10 cm long spikes with hairy pedicels, and ovate-oblong bracts with a ciliate margin. Each flower shows a pair of 2 bracteoles which are hairy, as long as the perianth, and 4 mm–5 mm long. The andrecium consists of 5 stamens. The fruits are utricles which are 3 mm in diameter (Fig. 65). Pharmaceutical interest: Achyranthes bidentata Bl. contains a series of oleanolic saponins which are probably responsible for the anti-inflammatory, diuretic and expectorant properties mentioned above. Note that ecdysterones characterized from Achyranthes bidentata Bl. promote the proliferation of osteoblast-like cells cultured in vitro (Gao XY et al., 2000). Achyranthes bidentata Bl. is also known to produce emodin and physcion, which are laxative anthraquinones (Bishit G et al., 1993). Other natural products characterized from this herb are Uses: Achyranthes bidentata Bl. is used to promote urination and expectatory resolve inflamed parts and as an astringent remedy. In Indonesia, chewing the fresh leaves with Areca catechu treats malignant mouth ulcers. In Malaysia, Achyranthes bidentata Bl. is used to treat extreme anemia. In Vietnam, the roots are chewed to promote salivation. The roots of Achyranthes bidentata Bl. are included in the Japanese Pharmacopoeia (dose 5 g to 8 g as a decoction).

Fig. 65. Achyranthes bidentata Bl.

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flavonoids glycosides: quercetin 3-O-rutinoside, quercetin 3-O-glucoside, kaempferol 3-O-glucoside, and caffeic acid (Nikolov S et al., 1995), which abound in antimicrobial, anti-inflammatory, free radicals scavenger properties and cytotoxic properties. Cytotoxic and antiviral properties: A methyl OH ester of achyranthoside characterized from O Achyranthes faurieri inhibits the proliferation of HO OH human colon carcinoma (IC50 = 5.2 µM) and murine melanoma (IC50 = 8.2 µM) cell-lines OH (Ida Y et al., 1994). Of recent interest is a series OH O of polysaccharides, characterized from the roots Quercetin of Achyranthes bidentata Bl. which inhibit the proliferation of sarcoma-180 cells and prolong the survival of Ehrlich carcinoma-bearing mice, by enhancing both specific and non-specific immunological responses (Xiang DB et al., 1993). An extract of Achyranthes bidentata Bl. causes the early expression of the Epstein-Barr (EBV) antigen in Raji cell-line (Zeng Y et al., 1994). Polysaccharides characterized from Achyranthes bidentata Bl. display anti-Herpes Simplex Virus 1 property in vitro and immunomodulatory effects (Li ZK et al., 1997; Zheng M et al., 1997). It will be interesting to know whether further investigation on oligosaccharides from Amaranthaceae will disclose any anti-viral molecule of therapeutic value. References Bishit G, et al. (1993) Fitoter 64(1): 85. Gao XY, et al. (2000) Yao Xue Xue Bao 35(11): 868–870. Ida Y, et al. (1994) Tetrahedron Lett 35(37): 6887–6890. Li ZK, et al. (1997) Yao Xue Xue Bao 32(12): 881–887. Nikolov S, et al. (1995) Int Symp Med Arom Plants, Amherst, Massachusetts, USA, 23–30 Aug. Xiang DB, et al. (1993) Chung-Kuo You Li Hsueh Pao 14(6): 556–561. Zeng Y, et al. (1994) Biomed Environ Sci 7(1): 50–55. Zheng M, et al. (1997) ZYY 32: 881–887.

Warning: Caution must be taken as the toxic effects of this plant are unknown. Alternanthera sessilis (L.) R. Br. [From Latin, alternus = every other and from Greek, anthos = flower and Latin sessilis = attached directly by the base] Physical description: It is an annual tropical herb with 20 cm–50 cm long, prostrate and many branched stems. The nodes are covered with long white

Synonymy: Alternanthera nodiflora R. Br., Telanthera amoena R. Br., Gomphrena sessilis. Common names: Carpet-weed; rumput aur, keremah bukit, kerumuk (Malay); pounanganni (Tamil); horngtyang wu (Taiwanese).

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hairs, and the internodes with a pair of longitudinal whorls of hairs. Leaves: 2 cm–6 cm, obtuse at the apex, remotely crenate and subsessile. The inflorescences are axillary, globose and sessile white heads, with very small bracts and bracteoles. The flowers comprise of a 5-lobed perianth, each lobe is 2 mm– 2.5 mm long and glabrous, consisting of 3 stamens and a few staminodes, hence the name of the genera. The fruits are obcordate and of obtusely margined utricles (Fig. 66). Pharmaceutical interest: Hepatoprotective property : The hepatoprotective property of Alternanthera ses- Fig. 66. Alternanthera sessilis (L.) R. Br. silis (L.) R. Br. is substantiated in rodent poisoned experimentally with carbon tetrachloride (31.25 µL/Kg, i.p.), paracetamol (600 mg/Kg, i.p.) and β-D-galactosamine (188 mg/Kg). In all the cases, the ingestion of the plant (300 mg/Kg) lowers the elevation of the serum levels of glutamate oxalic acetic transaminase [aspartate aminotransferase] Uses: In Indonesia: a decoction of Alternanthera sessilis (L.) R. Br. is (SGOT) and glutamate pyruvic acid drunk to stop dysentery and transaminase [alanine aminotransfediarrhea. In Malaysia, the plant is rase] (SGPT) enzymatic activities, as used to heal wounds and applied to well as improve the histopathologipainful areas. A decoction of 30 g of cal diagnosis of liver tissues (Lin SC the whole plant is drunk by Malays to et al., 1994). Although the natural prodstop dysentery, relieve the bowels of ucts responsible for the hepatoproteccostiveness, treat jaundice, fever, tive property of Alternanthera sessilis urinary tract infection, tuberculosis (L.) R. Br. are yet unknown, one and peptic ulcer, resolve sore throat must think of choline, which has been and intestinal inflammation, and to characterized from the South Amermitigate toothache. In Taiwan, Alternanthera sessilis (L.) R. Br. is ican medicinal Alternanthera pugens used to treat kidney diseases and (De Ruiz REL, 1993). As a matter of haemoptysis, and to fight depression. fact, choline is one of the B-complex vitamins essential for the metabolism of fats in the liver. Combined deficiency of choline and other methyl group donors cause hepatic cirrhosis. Choline is a precursor of methionine, used to counteract paracetamol poisoning. Cholinergic property : An aqueous extract of whole Alternanthera pugens contracts dose-dependently isolated portions of rabbit duodenum and

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increases the mobility of gastrointestinal muscles in mice on possible account of choline (Garcia SB et al., 1995). Choline is the precursor of acetylcholine, a neurotransmitter synthesized in the cholinergic nerve terminals by choline acetyltransferase. The binding of H3C + OH acetylcholine, released by presynaptic membranes to N C H 3 the muscarinic-receptors of the gastrointestinal smooth CH3 muscles, commands contraction, peristalsis of the Choline smooth muscle and release of the gastric juice. An ethanolic extract of Alternanthera pugens, given to rats, displays a diuretic property comparable to the commercial furosemide (Lasix® ; Calderon CP et al., 1997). Antiviral property: Amaranthaceae have attracted a great deal of interest because of their antiviral properties which are probably due to polysaccharides. An aqueous extract of Alternanthera philoxerioides inhibits the proliferation of the Human Immunodeficiency Virus (Zhang SM et al., 1988) and the proliferation of the Haemorrhagical Fever Virus (Yang ZQ et al., 1989). Alternanthera brasiliana, Alternanthera ficoidea and Amaranthus spinosus L. inhibit the proliferation of the Aujeszky Virus in IB-RS-2 pig cell-line and the proliferation of the Bovine Diarrhea Virus in GBK bovine cell-lines (Koseki I et al., 1990). An aqueous extract of Alternanthera brasiliana inhibits the proliferation of the Herpes Simplex Virus in vitro (Lagrota MHC et al., 1994). References Calderon CP, et al. (1997) Phytother Res 11(8): 606–608. De Ruiz REL, et al. (1993) Fitoter 64(1): 95. Garcia SB, et al. (1995) Fitoter 66(4): 324–327. Koseki I, et al. (1990) Microbios Lett 44(173): 19–30. Lagrota MHC, et al. (1994) Phytoter Res 8(6): 358–361. Lin SC, et al. (1994) Phytoter Res 8(7): 391–398. Yang ZQ, et al. (1989) 14(8): Chung-Kuo-Chung-Yao-Tsa-Chih, 488–490. Zhang SM, et al. (1998) Chin Med J Engl 101(11): 861–866.

Warning: Caution must be taken as the toxic effects of this plant are unknown. Aerva lanata (L.) Juss. [From Arabic, erwa = Aerva lanata (L.) Juss. and from Latin, lanatus = woolly] Physical description: It is a common tropical herb which grows to a height of 90 cm. The stems are terete and woolly. Leaves: simple, alternate, without stipules, and 1.8 cm–4 cm × 3 cm–4 mm. The blade is elliptic, obovate, obtuse or

Synonymy: Achyranthes lanata L.; Aerva floribunda Wight. Common names: Wool plant; astmabayada (Sanskrit); sirupulai (Tamil).

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acute, entire, pubescent above, and more or less woolly beneath. The petiole is short. The flowers are white or greenish and packed in small, dense, axillary, and woolly 5 mm–1 cm long heads or spikes, forming globose clusters. In these heads, the bracteoles are ovate and very small. The perianth consists of woolly, small and oblong sepals.The stamens are united into a tube with interposed staminodes shorter than the filaments, and the ovary is subglobose, and develops upward into a very small style and 2 stigmas. The fruits are very small utricles, containing a few subreniform, black, smooth and glossy seeds (Fig. 67). Pharmaceutical interest: The antiinflammatory and antidiabetes properties of Aerva lanata (L.) Juss. mentioned above are probably due to saponins or flavonoids glycosides. An aqueous extract and the fresh juice expressed from Aerva lanata (L.) Juss. inhibits carrageenan-induced edema in rodent (Amin KMY et al., 1994) and an ethanolic extract of the plant protects rodent against alloxan poisoning (Vetrichelvan T et al., 2002).

Fig. 67. Aerva lanata (L.) Juss.

Uses: In Indonesia, an infusion of Aerva lanata (L.) Juss. is used to treat sudden swollen areas. In the Philippines, an infusion of Aerva lanata (L.) Juss. is drunk to promote urination and to treat gonorrhea. In India, healers use Aerva lanata (L.) Juss. to treat renal and prostate ailments, as well as diabetes.

Of particular interest is canthine-6-one, characterized N from Aerva lanata (L.) Juss., which may contribute to the antimicrobial and antitumoral properties displayed by a crude methanolic extract of this herb (Chowdhury D et al., N 2002; Zapesochnaya GG et al., 1997). The presence of canthine-6-one in this plant is somewhat surprising O and should stimulate further research on the psychotropic potential. Note that canthine-6-one is known to occur in Canthine-6-one members of the order Sapindales (Subclass Rosidae). Narcissin (isorhamnetin-3-rutinoside), aervitrin (isohamnetin-3-rhamnosyl rutinoside), and a small amount of ecdysterone were characterized from Aerva lanata (L.) Juss. (Baltaev VA et al., 1992; Pervykh LN et al., 1992).

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References Amin KMY, et al. (1994) 4th Congress Ethno Lucknor Uttar Pradesh, India, 17–21 Nov. Baltaev VA, et al. (1992) Chem Nat Comp 28(5): 123–124. Chowdhury D, et al. (2002) Fitoter 73(1): 92–94. Pervykh N, et al. (1992) Chem Nat Comp 28(5): 509–510. Vetrichelvan T, et al. (2002) J Ethnopharmacol 80(2–3): 103–107. Zapesochnaya GG, et al. (1992) Planta Med 58(2): 192–196.

Warning: Caution must be taken as the pharmacological potential of this plant is unknown. Amaranthus spinosus L. [From Greek, amarantos = everlasting and anthos = flower and from Latin, spina = thorn] Physical description: It is a tropical, invasive and prickly herb which grows to a height of 1 m. The stems are succulent and ribbed. Leaves: simple, 2 cm–8 cm × 6 mm–4 cm, without stipules and with 1 cm–2 cm long thin prickles in the leaf axis. The petiole is long and thin. The blade is oblong and oval, blunt at the apex with a very small hair-like top, and a narrow base. The flowers are very small and arranged in dense axillary or terminal spikes, developing sharply pointed bracts as long as, or longer than the 5 perianth lobes. The andrecium consists of 5 stamens. The fruits are very small and contain a few glossy dark seeds (Fig. 68). Pharmaceutical interest: The pharmacological potential of Amaranthus spinosus L. remains unknown, although a host of evidence suggests that Amaranthus plants are likely to hold antiviral and anticancer properties. Amaranthus spinosus L., Alternanthera brasiliana and Alternanthera

Common names: Prickly amaranth, prickly blite, prickly pigweed; amaranthe epineuse, blette epineuse, brede malabar (French); mullukkirai (Tamil); hinnu nwe subank (Burmese); alpamarisha (Sanskrit); phti ach mon (Cambodian), bayam berduri (Malay). Uses: In the Asia-Pacific, Amaranthus spinosus L. is principally used internally to promote urination. In Cambodia, the roots are used to treat rheumatism and fever, and these are added to mustard plasters to treat uterine tumors. In Indonesia, the roots of Amaranthus spinosus L. are used to stimulate menses and its crushed leaves are used to heal festering wounds. In Malaysia, Amaranthus spinosus L. is used to promote urination whereas a decoction of the roots is drunk to promote expectoration and to stimulate menses. The leaves are used internally to treat bronchitis and externally to heal boils. In the Philippines, its crushed leaves are applied to eczematous areas. In Vietnam, Amaranthus spinosus L. is used to promote milk secretion and urination and a poultice of the powdered leaves is applied to heal dog bites. In India, the roots of Amaranthus spinosus L. are used to treat gonorrhea, menorrhagia and eczema.

Subclass Caryophyllidae

ficoidea inhibit consistently the proliferation of the Aujeszky Virus in IB-RS-2 pig cell-line and the proliferation of the Bovine Diarrhea virus in GBK bovine cell-line (Koseki I et al., 1990). An aqueous extract of Amaranthus spinosus L. contracts isolated rat uterine smooth muscles (Ayeh Tan et al., 1995). An extract of Amaranthus cruentus inhibits the proliferation of colon and gastric carcinoma cells (Lee J et al., 1996). Wistar albino rats fed with the seeds of Amaranthus aesculentus develop hypocholesterolaemia (Chaturvedi A et al., 1993). Note that triterpenoid saponins may be responsible for medicinal properties of Amaranthus spinosus L. (see Achyranthes aspera).

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Fig. 68. Amaranthus spinosus L.

An interesting feature of Amaranthus species is that they contain cysteine-enriched antifungal proteins (Cammue BPA et al., 1993) and antimicrobial chitin-binding proteins (Bole MFC et al., 1993). A number of glycoproteins (lectins) are useful tools in antigen-based diagnostic techniques. For example, amaranthine, a lectin characterized from Amaranthus caudatus, binds to the Thomsen-Friedemreich antigens which indicate foci of abnormal proliferation in familial colorectal cancer syndrome (Boland CR et al., 1991). References Boland CR, et al. (1991) Cancer Res 51(2): 657–665. Cammue BPA, et al. (1993) Work Eng Plants Pests Path 28–29. Chaturvedi A, et al. (1993) Plant Food Hum Nutr 44(1): 63–70. Koseki I, et al. (1990) Microbios Lett 44(173): 19–30. Lemos RA, et al. (1993) Pesq Vet Bras 13(1–2).

Warning: Amaranthus spinosus L. is edible and sold in Asian markets instead of spinach, but it causes anorexia, weight loss, diarrhea, petechiae, digestive hemorrhage and renal failure, if grown in highly nitrate fertilized lands (Lemos RA et al., 1993). Celosia argentea L. [From Greek, kelos = burned and from Latin, argentum = silver] Physical description: It is an annual tropical herb which grows to a height of 1 m in drains, vacant plots and by the roadside. The stems are terete and the upper part is often branched. Leaves: simple, 5 cm–8 cm × 1 cm–3 cm, alternate, and without stipules.The blade is lanceolate, ovate and sessile or not.The

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Synonymy: Celosia argentia, Celosia cristata. Common names: Wild cockscomb, Bombay yellow gold; cresta de gallo, borlas (Spanish); barhichuda (Sanskrit); bayam (Malay); kyetmonk (Burmese); chi kuan (Chinese); palonpalongan (Filipino).

apex is acute or acuminate, and the base is attenuate. The inflorescences are terminal and pinkish or white, 5 cm–8 cm × 1 cm–2.5 cm spikes. The flowers are 8 mm–10 mm × 2 mm, and comprise of a perianth of 5 lanceolate lobes and 5 stamens. The fruits are globose, and the circumscissile utricles containing a few black glossy seeds (Fig. 69).

Fig. 69. Celosia argentea L.

Pharmaceutical interest: Diuretic properties: Ethanol extracts of leaves and seeds inhibit the growth of bacterial burn pathogens cultured in vitro (Gnanamani A et al., 2003), protect rodents against alloxan poisoning (Vetrichelvan T et al., 2002) and promote urination in rodents as efficiently as hydrochlorothiazide (5 mg/Kg) standard. The seeds of Celosia argentea L. given per os (4 g) to 10 healthy human volunteers (male, 33–35 years old), increase significantly the secretion of urine (57%; Shah MB et al., 1993). Celosian: Of particular interest is the fact that an aqueous extract of seeds of Celosia argentea L. given intraperitonneally to animals infected with colon 26-L5 carcinoma cells, reduces significantly liver metastasis through the induction of cytokins (Hayakawa Y et al., 1998). From this extract was characterized the celosian, which is an immunostimulating and hepatoprotector acidic polysaccharide. Celosian inhibits the elevation of GPT, GOT and bilirubin in carbon tetrachloride-induced liver injury in rats and suppresses mortality on fulminant hepatitis caused

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by β-D-galactosamine/lipopolysaccharide or caused by Propionibacterium acnes/(LP5) in mice. Dose-dependent protection against chemical and immunological hepatitis is observed (Hase K et al., 1996). Celosian stimulates the production of tumor necrosis factor α (TNFα), 1β and nitric oxide in macrophage cell-line (1774-1) in a concentration-dependent manner, and promotes the secretion of interleukin Uses: Celosia argentea L. is used to 1β in human mononuclear cells. treat hematological and gynecologic Celosian enhances the production of diseases, to resolve inflammation and interferon γ by concavalin A in mouse to counteract putrefaction. In spleen cells (Hase K et al., 1997). Other pharmacological properties:The plant is also interesting because it produces a series of cyclic peptides, including celogentin A–C, and K which inhibit the polymerization of tubulin (Kobayashi J et al., 2001; Suzuki et al., 2004). The aerial part of Celosia argentea L. abound with flavonoids which may participate in the anti-inflammatory properties mentioned above. An extract of Celosia argentea L. examined on antiDNPantibody response in mice suppresses the secretion of IgE antibody in certain allergic disorders (Imago K et al., 1994). An aqueous extract of Celosia argentea L. displays an uterotonic property on isolated portions of rabbit and guinea-pig uterine horns (Shipochliev T, 1981).

Indonesia, the flowering tops are used to check bleeding of the lungs. In Malaysia, a decoction of the red flowering tops is drunk to check white discharges, dysentery, bleeding of the mouth and nose, piles, to regulate menses, and to remove blood and proteins from urine. The whole plant is used to stop dysentery, regulate urination, heal broken bones, wounds and abscesses, and to resolve swollen parts. A paste made from the seeds is used to heal broken bones. The seeds are used to treat conjunctivis and to lower blood pressure. In Cambodia, Laos and Vietnam, a lotion made from the seeds is applied to soothe inflamed eyes. In China, the seeds are used to stop hemorrhage and menorrhagia, and to treat ophthalmia. In India, the seeds are eaten to treat diabetes.

References Gnanamani A, et al. (2003) J Ethnopharmacol 86(1): 59–61. Hayakawa Y, et al. (1998) Biol Pharm Bull 21(11): 1154–1159. Hase K, et al. (1996) Biol Pharm Bull 19(4): 567–572. Hase K, et al. (1997) Planta Med 63(3): 216–219. Kobayashi J, et al. (2001) J Org Chem 66(20): 6626–6633. Imakoa K, et al. (1997) Arerugi 43(5): 652–659. Shah MB, et al. (1995) Int J Pharmacog 31(3): 223–234. Shiposliev T, et al. (1981) Vet Med Nauki 18(4): 94–98. Suzuki H, et al. (2004) Tetrahedron 60(11): 82489–2495. Vetrichelvan T, et al. (2002) Biol Pharm Bull 25(4): 526–528.

Warning: Caution must be taken as the toxic effects of this plant are unknown.

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Cyathula prostrata (L.) Bl. [From Greek, cyathos = a cup and from Latin, sternere = lay flat] Synonymy: Achyranthes prostrata L., Pupalia prostrata Mart. Common names: Cyathula; mata kura (Cook Islands); tolomo’unga (Tonga); yaa phannguu daeng (Thai); dayang (Filipino).

Physical description: It is a prostate and hairy herb which grows to a height of 1 m in a geographical zone spanning Africa, China, Australia and the Pacific Islands. The stems are round, articulate and swollen at the nodes. Leaves: opposite, without stipules, and 6.5 cm × 2.5 cm–2 cm × 8 cm. The blade is lanceolate, asymmetrical, 5 cm–2.5 cm × 1.5 cm–8 mm and the margin is entire and slightly wavy. The midrib is raised above and below, and the blade shows 5–6 pairs of secondary nerves. The inflorescences consist of terminal 2 mm long spikes of scaly flowers (Fig. 70).

Uses: In China, the stems and leaves are used to relieve the bowels of costiveness. In Indonesia, the plant is used to treat cholera, fever, and bowel looseness. In Malaysia, the plant is applied externally to expel intestinal worms and to treat some skin affections. In the Philippines, the plant is used to facilitate digestion. In Taiwan, a decoction of the leaves is used to wash snake bites, and the roots are used to treat rheumatism, liver problems, dysentery, fever and dropsy.

Pharmaceutical interest: The medicinal properties of Cyathula prostrata (L.) Bl. remain unexplored. Note that this plant would be worth studying as Fig. 70. Cyathula prostrata (L.) Bl. a fructan of the graminan type characterized from Cyathula officinalis Kuan inhibits the growth of Lewis pulmonary carcinoma implanted in mice (Chen XM et al., 2003). Reference Chen XM, et al. (2003) Carbohydr Res 338(11): 1235–1241.

Warning: Caution must be taken as the toxic effects of this plant are unknown.

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Deeringia amaranthoides (Lamk.) Merr. [After Georg Karl Deering, an English doctor, and from Latin, amaranthoides = amaranth-like] Uses: In Indonesia, the juice squeezed from the roots is used as an ingredient of a mixture which is sniffed to clear congested nasal cavities. The leaves are used to treat inflamed sores and chicken pox maturations. In the Philippines, a decoction of the leaves is drunk to treat dysentery. In the Solomon Islands, the sap expressed from the plant is used to counteract skin putrefaction in pigs. The therapeutic potential of this plant is still yet to be discovered. A number of oleanolic saponins were characterized from the fruits (Sati OP et al., 1990) and might be involved in the medicinal properties of this plant.

Synonymy: Achyranthes amaranthoides Lamk., Deeringia baccata Moq., Digera arvensis Forssk. Common names: Deeringia.

Physical description: It is a sprawling shrub which grows in the geographical zone spanning India to the Pacific Islands. The stems are terete and smooth. Leaves: simple, spiral, Fig. 71. Deeringia amaranthoides (Lamk.) 3.5 cm × 2 cm–16 cm × 7 cm and with- Merr. out stipules. The petiole is 1.7 cm– 4 cm long and thin. The blade is papery, asymmetric and 3.8 cm–2.2 cm × 6 cm×12.5 cm.The apex is somewhat acuminate, the base is acute and asymmetrical and the margin is entire or serrulate. The midrib is sunken above and raised below, and the blade shows 4–8 pairs of secondary nerves. The inflorescences are terminal spikes. The flowers are very small and comprise of 5 bracts, 5 stamens and a pyriform gynecium. The fruits are juicy, red and glossy (Fig. 71). Reference Sati OP, et al. (1990) J Nat Prod 53(2): 466–469.

Warning: Caution must be taken as the toxic effects of this plant are unknown.

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Gomphrena globosa L. [From Latin, gomphaena = amaranth and globulus = globe] Physical description: It is an ornamental, hairy and upright herb native to South America which grows to a height of 30 cm in several tropical countries. Leaves: opposite, simple, without stipules and 5 cm–10 cm long. The flowers are small and compressed into globose and terminal heads of 2.5 cm– 4 cm in diameter, comprising of several rose, pink or white magenta bracts.The flowers consist of 5 lanceolate, acuminate and woolly sepals. The fruits are indehiscent utricles containing 1 round seed (Fig. 72).

Common names: Globe amaranth, bachelor’s buttons; bunga butang (Malay).

Pharmaceutical interest: The therapeutic potential of Gomphrena gloFig. 72. Gomphrena globosa L. bosa L. is still waiting to be discovered and would be worth assessing as a number of experiments conducted in vitro tend to demonstrate antimicrobial, molluscicidal and cytotoxic properties from the Gomphrena species. Cytotoxic properties: A crude petrolUses: In Malaysia, a decoction of eum ether fraction of Gomphrena marthe flowers of Gomphrena globosa L. tiana and Gomphrena boliviana, two is drunk to treat asthma, bronchitis plants traditionally used in Argentina and leucorrhea, check hemorrhage to treat cancer, inhibit the proliferaand nocturnal weeping of children and tion of sarcoma-180 tumors in mice to soothe sore eyes. The fresh plant is (Pomilio AB et al., 1991). The active boiled or macerated and applied to traumatic injuries and pyoderma. principle of Gomphrena martiana is a lipophilic 5, 6, 7-trisubstituted flavone (Pomilio AB et al., 1994) which also inhibits Mycobacterium phlei proliferation in vitro (Pomilio AB et al., 1992). Antimicrobial properties: An aqueous extract of Gomphrena celosioides inhibits the proliferation of Staphylococcus aureus, Streptococcus pyogene, Escherichia coli, Salmonella thyphi, Shigella dysenteriae, Pseudomonas aeruginosa and Candida albicans cultured in vitro (Souza de C et al., 1993). An extract of the roots of Gomphrena macrocephala inhibits the proliferation of adult snails of Biomphalaria glabrata (Yamamoto MM et al., 1996). Recent investigations on Gomphrena globosa indicate the presence of saponins in

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the seeds which inhibit significantly (IC50 = 3.5 µg/mL) the formation of interleukin6 by osteoblastic cells (MC3T3-E10) without cytotoxicity in vitro. This property could be useful for the treatment of chronic rheumatoid arthritis, infection, cancer inflammation and osteoporosis. References Pomilio AB, et al. (1991) Fitoter 62(6): 511–514. Pomilio AB, et al. (1992) J Ethnopharmacol. 36(2): 155–166. Pomilio AB, et al. (1994) J Ethnopharmacol 44(1): 25–33. Souza de C, et al. (1993) Rev Med Pharmacop Afr 7(2): 109–115. Yamamoto MM, et al. (1996) Fitoter 67(1): 59–62.

Warning: Caution must be taken as the toxic effects of this plant are unknown.

5. Family MOLLUGINACEAE Hutchinson 1926, nom. conserv., the Carpet - weed Family Physical description: The family Molluginaceae consists of about 13 genera and nearly 100 species of herbs found mainly in tropical and subtropical regions. This family and the family Caryophyllaceae are very close to each other and have both evolved from a ranunculaceaous ancestor. Both Molluginaceae and Caryophyllaceae are strongly hypogynous with distinct sepals and petals, and abound with triterpenoid saponins. The leaves of Molluginaceae are simple, opposite, alternate or whorled, with or without stipules. The inflorescences are cymes of little flowers which are hermaphrodite and regular. The flowers comprise of 4–5 sepals, persistent and free, and small petals. The andrecium comprises of 2–10 stamens, the filaments of which are free or variously connate at the base, and the anthers of which are tetrasporangiate, dithecal and open by longitudinal slits. The gynecium consists of 2–5 carpels which are united to form a compound, superior ovary with a distinct style. The ovary encloses a single to many ovules which are attached to axillary placentas. The fruits are capsules opening loculicidally or by transverse slits, are rarely indehiscent and commonly surrounded by a persistent calyx. The seeds are kidney-shaped and arillate. Pharmaceutical interest: It will be interesting to learn whether or not more intensive future research will disclose any molecules of therapeutic interest from Molluginaceae. Most of the medicinal Molluginaceae used in the Asia-Pacific are part of the genus Mollugo: Mollugo pentaphylla L. (Mollugo stricta L.), Mollugo hirta Thunb. (Glinus lotoides L.), and Mollugo oppositifolia L. (Glinus oppositifolius (L.) A. DC., the properties of which are often attributed to saponins.

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Mollugo pentaphylla L. [From Latin, Mollugo = an old name for the genus Galium, and from Greek, pente = five and phullon = leaf] Synonymy: Mollugo stricta L. Common name: Mollugo, Indian chickweed.

Physical description: It is an annual tiny weed found in the sandy coasts of China, Malaysia, Japan, Korea, China Solomon Islands and India, which grows to a height of 30 cm. Leaves: simple, 7 mm × 1.5 cm and whorled in groups of 2–5 at nodes. The petiole is indistinct, and the blade is the lanceolate and very thin. The flowers are very small, whitish and arranged in terminal or axillary inflorescences.The fruits are dehiscent capsules of 2 mm diameter with persistent sepals, containing black, 0.5 mm diameter kidneyshaped and microscopically muricate seeds (Fig. 73). Pharmaceutical interest: One might set up the hypothesis that the healing properties mentioned above could be attributed to pentacyclic triterpenes. One such terpene is mollugogenol A, characterized from the aerial part of Mollugo pentaphylla L. as

Fig. 73. Mollugo pentaphylla L.

Uses: In China, the plant is used to promote appetite and to treat eye diseases. In Malaysia, a paste of Mollugo pentaphylla L. is used to heal sores. In the Solomon Islands, the plant is burned to make smoke that repel mosquitoes.

OH OH HO OH Mollugogenol A

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121

an antifungal principle, on account of the membrane damage as observed in spermatozoids (Hamburger M et al., 1989, Rajasekaran M et al., 1993). Other natural products characterized from Mollugo pentaphylla L. are flavones (Chopin J et al., 1982; Jha OP et al., 1984) References Chopin J, et al. (1982) Phytochem 21(9): 2367–2370. Hamburger M, et al. (1989) Phytochem 28(6): 1767–1768. Jha OP, et al. (1984) J Indian Chem Soc 61: 193–194. Rajasekaran M, et al. (1993) Contraception 47(4): 401–412.

Warning: Caution must be taken as the toxic effects of this plant are unknown.

6. Family CARYOPHYLLACEAE A. L. de Jussieu 1789 nom. conserv., the Pink Family The Caryophyllaceae is a large family which consists of about 75 genera and 2000 species of cosmopolitan, annual or perennial herbs which abound with pentacyclic triterpenoid saponins. Caryophyllaceae are easily recognized in a field collection by their heart-shaped interpetiolar internodes. The leaves of Caryophyllaceae are simple and opposite, with stipules or without stipules. The flowers are actinomorphic, hypogynous, bisexual and commonly arranged in dichasial cymes or are solitary. The calyx comprises of 5 sepals which are free or form a tube. The corolla, if present, comprises of 5 petals. The andrecium consists of 5–10 stamens arranged in 1 or 2 whorls, with free filaments and tetrasporangiate and dithecal anthers opening by longitudinal slits. The gynecium is made of 2–5 carpels, forming a superior, sessile or shortly stipitate, single-celled or imperfectly divided ovary containing a central placenta, and developed upwards into free or connate styles. The fruits are dehiscent capsules opening by valves or apical teeth. The seeds are finely punctuated and curved. Pharmaceutical interest: Belonging to the family Caryophyllaceae are a large number of herbs cultivated for decorative purposes such as Dianthus barbatus L. (pink, sweet William), Gypsophila elegans Bieb. (baby’s breath, gypsophila) and Dianthus caryophyllus L. (carnation). Classical medicinal Caryophyllaceae are Saponaria officinalis L. (soapwort, bouncing bet, Fuller’s herb), Quillaja saponaria Molina and Gypsophila paniculata (maiden’s breath). A decoction of the dried root of Saponaria officinalis L. (1 in 29; dose 15 mL– 30 mL) has been used in Western medicine to promote expectoration and urination. Quillaja saponaria Molina. is occasionally used to make shampoo and is known to inhibit the intestinal absorption of cholesterol. Most medicinal Caryophyllaceae owe their properties to triterpenoid saponins, which are surface-acting agents and quite often irritating for mucosa. More interesting

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COOR2 OH R1-O CHO R1: glucuronic acid, xylose, galactose R2: fucose, acyl, xylose, apiose, rhamnose, glucose

Pentacyclic triterpenoid saponins of Caryophyllaceae: Quillaja saponin

are the hormonal potency of saponins aglycones and the immunomodulating and even antiviral property of a number of oligosaccharides or polysaccharides characterized from them. Nearly 30 species of Caryophyllaceae are used for medicinal purposes in the Asia-Pacific. Most of these are used internally to check hemorrhages, depurate, treat fever, promote milk secretion, abortion, delivery, urination and menses, and externally to remove malignant sores and to counteract putrefaction. Drymaria cordata Willd. [From Latin, cordis = heart] Physical description: It is an annual Synonymy: Holosteum cordatum L.; invasive weed native to Central Drymaria cordata subsp. diandra America which grows to a height of (Blume) J. A. Duke; Drymaria diandra 90 cm in damp shaded sites, often Blume. near streams or under shrubs, and Common names: Drymaria, West other open fields. The stems are Indian chickweed, tropical chickweed, straggling, sometimes sub-scandent, whitesnow; mourron blanc (French); angled, usually rooting at the lower pipili, pilipili (Hawaii); he lian dou cao nodes and hairy toward inflorescence. (Chinese). Leaves: simple and opposite. The stipules are membranous, splitting into a few whitish setae. The petiole is 1 mm– 2 mm long and channeled.The blade is papery, 1.2 cm×2.5 cm–1.6 cm×9 mm, glabrous, and kidney-shaped to cordate. The midrib is raised below. The blade shows 2 pairs of secondary nerves. The apex of the blade is round or obscurely acuminate, and the margin is entire. The inflorescences are cymose and the flower pedicels are 3 mm–5 mm long and covered with whitish hairs. The flowers are small and white. The calyx comprises of 5, 3-veined, glandular sepals which are lanceolate ovate, 2 mm–3.5mm long and hairy. The corolla consists of 5 lanceolate, 2.5 mm long petals which

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are deeply bifid and pure white. The andrecium comprises of 2–5 stamens which are shorter than the sepals. The gynecium consists of 3 styles connate at the base and is greenish yellow. The fruits are capsular, 2 mm–3 mm long, 3-valved and contain several dark brown, suborbicular, 1.5 mm long and regularly densely tuberculate seeds (Fig. 74). Pharmaceutical interest: A methanol extract of Drymaria cordata Willd. displays a significant antitussive activity in a sulphur-dioxide cough-induced experiment, as efficiently as codeine phosphate (Mukherjee PK et al., 1997). Note that this plant contains saponins and cyclic peptides (Yuan AX et al., 1987; Ding Z et al., 2000), the former being probably responsible for the antitussive property. It will be interesting to learn whether more intensive future research on the cyclic peptides of Drymaria cordata Willd will disclose any molecules of chemotherapeutic interest.

Fig. 74. Drymaria cordata Willd. From: KLU Herbarium 21641. Field collector & botanical identification: J. B. Lowry, 30 Nov 1974. Geographical localization: Boh Tea Estate, Cameron Highlands, Malaysia.

Uses: In Indonesia, a paste made from the aerial part of Drymaria cordata Willd. mixed with lime is applied externally to counteract skin putrefaction. Indonesians drink the juice expressed from this plant to relieve the bowels of costiveness and to treat fever. In Papua New Guinea, Drymaria cordata Willd. is used to invigorate health. In Taiwan, a paste made from the aerial parts is applied externally to counteract snakepoisoning.

References Ding Z, et al. (2000) Planta Med 66(4): 386–388. Mukherjee PK, et al. (1997) J Ethnopharmacol 56(1): 77–80. Yuan AX, et al. (1987) Chung Yao Tung Pao 12(1): 36–37.

Warning: Irritant and possibly allergenic properties have been ascribed to saponins in members of Caryophyllaceae. The toxic effects of this herb are unknown and its consumption is therefore hazardous.

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Polycarpaea corymbosa Lamk. [From Greek, polus = many, karpos = fruit and korumbos = cluster] Synonymy: Achyranthes corymbosa L. Common names: Old man’s cap; pai t’ou weng; bai gu ding (Chinese); pak thow yoong (Malay); bhisatta (Sanskrit); nilaisedachi (Tamil).

Uses: The inflorescences of Polycarpaea corymbosa Lamk. are sold in the Chinese pharmacies of Cambodia, Laos, Vietnam and Malaysia as an emollient and as astringent drugs. In India, Polycarpaea corymbosa Lamk. is used to treat strangury, urinary stones, inflammation, swollen parts and ulcers. Its ashes mixed with pepper is used to heal boils and ulcers (Ayurveda). Its pounded leaves are applied to boils and inflamed parts. The therapeutic potential of Polycarpaea corymbosa Lamk. remains unexplored.

Physical description: It is a herb native to Africa which grows to a height of 45 cm. It is found throughout the tropics and subtropics, mostly on open, often moist, sandy soils, less often in grassy places on mountain slopes; from sea level to 1200 m. The stems are corymbose and slender, and the young ones are woolly. Leaves: simple, 8 mm–2 cm long, narrow linear and mucronate. The stipules are lanceolate, acute and single-nerved. The flowers are numerous and small, and arranged in dense, much branched, terminal cymes forming flat-topped heads. The pedicels of the flowers are woolly, and the bracts are 3 mm long, silvery-white, and bristle. The sepals are lanceolate, acute, 2 mm– 4 mm long, scarious, membranous, hyaline, silvery-white, and much longer than both the petals and capsules. The petals are milky white or reddish, and broadly ovate. The andrecium consists of 5 stamens which are shorter than the petals. The gynecium comprises of a short style. The fruits are brown and ovoid capsules containing 5–13 glossy, flat and brown obscurely reticulate seeds which are 0.3 mm–0.5 mm in diameter (Fig. 75). Warning: Caution must be taken as the toxic effects of this plant are unknown.

Fig. 75. Polycarpaea corymbosa Lamk.

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125

Saponaria vaccaria L. [From Latin, saponaria = soapy and vaccaria = cow herb] Physical description: It is an annual Synonymy: Vaccaria pyramidata herb which grows to a height of 60 cm. Medic., Saponaria perfoliata Roxb., It is found in temperate and subtropiGypsophila vaccaria. cal countries.The stems are somewhat Common names: Cow herb, cow pubescent. Leaves: 2.5 cm–6.3 cm × cockle, soapwort, perfoliate soapwort; 6 mm–2 cm, sessile, and glabrous.The gafis (Arabic); wang pu liu hsing lower ones are oblong-acute and the (Chinese); ble´ de vache, copatte, upper ones are oblong-lanceolate, saponaire a` vache (French); cetino very acute and mucronate.The flowers (Italian); vuong bat lieu hank are arranged in corymbose cymes with (Cambodia, Laos, Vietnamese). 2.5 cm–5 cm long pedicels and foliaceous bracts. The calyx is 1.2 cm long, ventricose in fruit, 5-nerved, scarious, and develops 5 teeth. The petals are rosy, obovate, and slightly emarginate. The claw of each petal is shortly exerted, and the limb is 1.2 cm long. The fruits are broadly ovoid capsules. The seeds are globose, black, and granulate. Pharmaceutical interest: Xanthones: To date, the pharmacologUses: Saponaria vaccaria L. is used ical potential of Saponaria vaccaria L. by the Chinese to heal furuncles and is unknown but the plant contains a wounds, soothe inflamed parts, and xanthone called vaccaxanthone. Xanto check bleeding. In Cambodia, Laos thones, have attracted a great deal of and Vietnam, Saponaria vaccaria L. is interest on account of their antifunused to expel impurities. In India, gal, antibacterial, platelet aggregation Saponaria vaccaria L. is used to reduce spleen enlargement, regulate inhibitors, anti-inflammatory and antimenses, heal ulcers, and to soothe Human Immunodeficiency Virus propinflamed parts and irritated skin. The erties as well as their ability to inhibit juice expressed from the plant is used the enzymatic activity of monoamine to treat fever and to invigorate health. oxidase (MAO A and to a lesser of extent of MAO B). What are the pharmacological properties of vaccaxanthone? OH

O

OO

H

O OH

O OCH3 Vaccaxanthone

OH

126

Division MAGNOLIOPHYTA

Antitumor properties: Of particular interest are cytotoxic ribosome-inactivating glycoproteins characterized from Saponaria species. Examples of such glycoproteins are saporin 6 and pyramidatine (Gasperi-Campani A et al., 1991; Tecce R et al., 1991). The seeds of Saponaria vaccaria L. contain pyramidatine, which is able to bind covalently to the anti-epidermal growth factor receptor monoclonal antibodies, and therefore inhibit significantly the proliferation of grafted human tumor cells in nude mice (Di Massimo AM et al., 1997). References Di Massimo AM, et al. (1997) Br J Cancer 75 (6): 822–828. Gasperi-Campani A, et al. (1991) Anticancer Res 11(2): 1007–1011. Tecce R, et al. (1991) Melanoma Res 1(2): 115–123.

Warning: Caution must be taken as the toxic effects of this plant are unknown. Silene aprica Turcz. [From Latin, Silenus = the foster father of Bacchus and aprica = sunny] Synonymy: Melandrium apricum Rohrb., Melandrium firmum Rohrb. Common names: Sunward silene.

Physical description: It is a herb which grows to a height of 60 cm. It is found in Japan, China and Korea. The stems are terete and pubescent at the nodes, and brownish-yellow. Leaves: simple, opposite and without stipules. The blade is sessile, lanceolate-linear, sheathing at the base, recurved and obscurely ciliate at the margin, and shows a midrib sunken above and raised below, and a few indistinct pairs of secondary nerves. The inflorescences are axillary and terminal cymes of 1 cm × 5 mm flowers. The calyx is tubular, very thin and 5-lobed. The corolla comprises of 5 petals. The fruits are dehiscent capsules embedded in the very thin persistent calyx and contain a few 0.5 mm long, muricate and black seeds (Fig. 76).

Fig. 76. Silene aprica Turcz. From: KLU Herbarium 22534. Field collector & botanical identification: Tashiro, 16 May 1920. Geographical localization: Japan, Kyushu, Kagoshima Pref.: Kajiki.

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Pharmaceutical interest: One might Uses: In China, Silene aprica Turcz. set up the hypothesis that the medicis used to normalize blood circulation inal properties mentioned above are and to treat gonorrhea. In Korea, the attributed to triterpenoid saponins of plant is used to promote urination, the oleanane type which abound in the and to treat breast cancer and of lactation problems. plant (Glensk M et al., 1999; Saatov Z et al., 1990). Silene species are interesting because of their immunostimulating properties. Triterpene saponins characterized from Silene fortunei and Silene jenisseensis enhance granulocyte phagocytosis in vitro (Lacaille-Dubois MA et al., 1997; 1999) and polysaccharides from Silene vulgaris boost the immune system (Popov SV et al., 1999). Note that an infusion of Silene saxifraga is beneficial on urolithiasis in rats (Grases F et al., 1994). A 50% ethanol extract of Silene aprica protects the liver of rats against carbon tetrachloride-and acetaminophen-induced injuries (Ko YJ et al., 2002). Is choline involved here? References Glensk M, et al. (1999) J Nat Prod 62(5): 717–721. Grases F, et al. (1994) Int Urology Nephrology 26(5): 507–511. Ko YJ, et al. (2002) Am J Chin Med 30(2–3): 235–43. Popov SV, et al. (1999) International J Immunopharmacol 21(9): 617–624. Saatov Z, et al. (1990) Khim Prim Soedin 26(4): 405–407.

Warning: Caution must be taken as the toxic effects of this plant are unknown.

C. Order POLYGONALES Lindley 1833 The order Polygonales consists of a single family: the family Polygonaceae.

1. Family POLYGONACEAE A. L. de Jussieu 1789 nom. conserv., the Buckwheat Family Physical description: This large North Temperate family consists of about 30 genera and 1000 species of rhizomatous succulent, tanniferous and bitter-tasting herbs, commonly producing tannins, oxalic acid, flavonoids and anthraquinone glycosides. Polygonaceae are easily recognizable in the fields by their stipules which are well-developed and united into a sheath or ochrea which surrounds the stems. The stems are often hollow, zigzag-shaped, reddish, tabbed and juicy. The leaves of Polygonaceae are simple, stipulate, often aristate, soft and alternate. The flowers are very small, hermaphrodite or unisexual, and actinomorphic. The perianth consists of 2–6 tepals arranged in 1–several whorls. The andrecium comprises of 2–9 stamens principally

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Division MAGNOLIOPHYTA

arranged in 2–3 whorls, and the anthers are 2-celled and open lengthwise. The gynecium consists of 2–4, but principally 3 carpels united into a compound and 1-celled ovary, often triangular, which is attached to a nectary disc. The ovary develops upward 2–4, free styles and contains a solitary, basal and orthotropous ovule.The fruits are trigonous achenes containing a starchy seed. Pharmaceutical interest: Classical examples of OH O OH Polygonaceae are Fagopyrum esculentum Moench. (buckwheat, ble´ noir ), which is used in Brittany (France) to make delicious flat cakes, and Rheum raponthicum L. (garden rhubarb). A striking feaCH3 ture of Polygonaceae is the presence of both lanO thraquinone glycosides and tannins, the preponChrysophanol derancy of which will result in either laxative or/and antidiarrheal properties. For instance, the rhizomes of Rheum palmatum L. var. tanquticum Maxim. and Rheum officinale H. Bn. are laxative but in small doses the same rhizomes can stop diarrhea. Polygonum bistorta L., a tanniferous Polygonaceae, is used to stop diarrhea in Western medicine. Anthraquinone glycosides are laxative because they irritate the bowels and inhibit the active transfer of ions through the intestinal membranes. Anthraquinone glycosides decrease the resorption of water, sodium ions and chlorine ions by blockade of the sodium/potassium ATPase. Of recent interest is the discovery of resveratrol, a phenolic substance with chemopreventive properties in the Polygonum roots. In the Asia-Pacific, about 30 plant species of Polygonaceae are of medicinal value, mostly used to stop diarrhea, relieve bowels of costiveness, to expel intestinal worms, regulate menses, reduce liver discomfort, treat fever and skin infection, soothe inflammation and to invigorate health. Polygonum barbatum L. [From Greek, polus = many and gonos = angled, and from Latin, barbatus = bearded] Physical description: It is a perennial aquatic herb which grows to a height of 90 cm. It is found by the streamside, in wet areas, besides water and in the swamps of China, Taiwan, Bhutan, India, Myanmar, Nepal, the Philippines, Indonesia and Malaysia, from sea level to 1300 m. The stems grow from a rhizome, are reddish, pubescent, bitter and

Synonymy: Pericardia barbata (Linnaeus) H. Hara; Pericardia omerostroma (Ohki) Sasaki; Polygonum kotoshoense K. Ohki; Polygonum omerostromum Ohki. Common names: Knotweed; tebok seludang (Malay); mao liao (Chinese).

Subclass Caryophyllidae

sweet-sour-tasting. Leaves: simple, alternate and stipulate. The ochrea is tubular, 1.5 cm–2 cm long, membranous, and densely hispidulous. The petiole is 5 mm– 8 mm long and densely hispidulous. The blade is lanceolate or elliptic-lanceolate, 7 cm–15 cm × 1.5 cm–4 cm, and pubescent. The base of the blade is cuneate, the margin is ciliate, and the apex is acuminate. The inflorescences are terminal, spicate, erect, 4 cm–8 cm, and comprise of several spikes aggregated like panicles. The flowers are small and comprise of a white or greenish perianth made of 5 elliptic 1.5 mm–2 mm long lobes. The andrecium consists of 5–8 pinkish stamens. The gynecium comprises of 3 styles and a few capitate stigmas. The fruits are black, ovoid, trigonous, 1.5 mm–2 mm long shiny achenes included in the perianth (Fig. 77).

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Fig. 77. Polygonum barbatum L.

Pharmaceutical interest: Anti-inflammatory properties: An aqueUses: In Malaysia, the plant is used to ous extract of Polygonum punctatum invigorate health after childbirth and to given orally at 300,mg/Kg–600 mg/Kg expel intestinal worms. In Cambodia, to rats inhibits carrageenan-induced Laos and Vietnam, the seeds of oedema (Simoes CM et al., 1989). Polygonum barbatum L. are astringent This activity might be mediated by tanand used to treat cholera, stop nins or even resveratrol, characterized dysentery and to invigorate health. later from Polygonum sp., which inhibit experimentally the enzymatic activity of rat polymorphonuclear leukocytes lipooxygenase and cyclo-oxygenase (Kimura Y et al., 1985). Inhibitors of lipooxygenase and cyclo-oxygenase, key enzymes of the inflammatory process, are useful for treating inflammation. A classical example of cyclo-oxygenase inhibitor is aspirine, the forerunner of which is a natural product: salicin. Antiviral and antibacterial properties: An aqueous extract of Polygonum punctatum hampers the proliferation of Herpes Simplex Virus type1 cultured in vitro (Kott V et al., 1999). It would be interesting to find out the principles involved here. An aqueous extract of Polygonum capitatum decreases the death rate of mice

OH

HO OH Resveratrol

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Division MAGNOLIOPHYTA

O

O O

O

Stigmast - 4 - ene - 3, 6 dione

Stigmastane - 3, 6 - dione

O

O O

CH2OH OH

HO

O

F O

HO Hecogenin

Betamethasone

Fig. 78. Note the similitude of chemical structures of stigmast-4-ene-3, 6-dione, stigmastane-3, 6-dione, hecogenin and betamethasone.

experimentally infected with Escherichia coli, and the body temperature of infected rabbits (Ren G et al., 1995). References Kimura Y, et al. (1985) Biochim Biophys Acta 834(2): 275–281. Kott V, et al. (1999) J Ethnopharmacol 64(1): 79–84. Ren G, et al. (1995) Chung Kuo Chung Yao Tsa Chih 20(2): 107–109. Simoes CM, et al. (1989) J Pharm Belg 44(4): 275–284.

Warning: Caution must be taken as the toxic effects of this plant are unknown. Polygonum chinense L. [From Greek, polus = many and gonos = angled and from Latin, chinense = from China] Physical description: It is a perenCommon names: Mountain nial, rhizomatous herb which grows to knotweed, Chinese knotweed; huo tan a height of 1 m in wet valleys, mixed mu (Chinese). forests, thickets in valleys, and the grassy mountain slopes of China, Taiwan, the Himalayas, Japan, India, Malaysia and Philippines, from sea level to 3000 m. The stems are ligneous at the base, multi-branched, pinkish, striate, glabrous or hispid and sour-tasting.

Subclass Caryophyllidae

Leaves: simple and alternate. The ochrea is tubular, 1.5 cm–2.5 cm long, membranous, glabrous, veined and oblique at the apex. The petiole is 1cm–2 cm long, and auriculate at the base. The blade is ovate, elliptic or lanceolate, 4 cm–16 cm × 1.5 cm–8 cm, and glabrous or hispid. The base of the blade is truncate or broadly cordate. The margin is entire, and the apex of the blade is shortly acuminate. The Inflorescences are long and thin axillary clusters of very small flowers. The flowers are white or pinkish and comprise of a perianth made of 5 ovate lobes which are accrescent in fruits. The andrecium consists of 8 stamens with blue anthers. The gynecium includes 3 styles which are connate at the base. The fruits are broadly ovate, trigonous, black achenes included in the perianth (Fig. 79).

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Fig. 79. Polygonum chinense L.

Pharmaceutical interest: 25-R-spiroUses: In China, Polygonum chinense st-4-ene-3, 12-dione, stigmast-4-eneL. is used internally to stop dysentery, 3, 6-dione, stigmastane-3, 6-dione, expel impurities and to assuage hecogenin and aurantiamide acetate headache. The plant is applied characterized from this herb are antiexternally to the abdomen to assuage inflammatory and anti-allergic (Tsai PL stomachache. et al., 1998). Note the similitude of chemical structures of these steroids and the anti-inflammatory drug betamethazone (Fig. 78). Reference Tsai PL, et al. (1998) Phytochem. 49(6): 1663–1666.

Warning: Caution must be taken as the toxic effects of this plant are unknown.

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IV. Subclass DILLENIIDAE Takhtajan 1966 The subclass Dilleniidae consists of 13 orders, 78 families and about 25 000 species of woody plants which are thought to have originated from the Magnoliidae early in the Upper Cretaceous (Appendix I). Dilleniidae are mostly trees with showy flowers which are hermaphrodite, with united carpels, and adapted to insect pollination. The chemical weapons used in this subclass to repel herbivorous animals insects, plants and microorganisms are diverse. Of pharmaceutical interest in this subclass are coumarins and oligostilbenes (Theales), naphthoquinones (Nepenthales), cucurbitacins (Malvales and Violales) and naphthylisoquinoline alkaloids (Violales). The order Dilleniales is a little transitional group of 2 families and about 400 primitive plant species which connects Illiciales and Theales (Appendix I).

A. Order DILLENIALES Huntchinson 1926 Most species in Dilleniales belong to the family Dilleniaceae.

1. Family DILLENIACEAE Salisbury 1807 nom. conserv., the Dillenia family Physical description: The family Dilleniaceae consists of 10 genera and about 350 species of tropical trees, shrubs, climbers and herbs which are best developed in Australia. Dilleniaceae are so far known to abound with tannins and saponins. Note that flavonols (myricetin) and occasionally benzylisoquinoline alkaloids are also known to occur in the family. The family Dilleniaceae is thought to connect Magnoliidae to the Dilleniidae. One must have probably observed the

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botanical similitude between Illiciaceae (subclass Magnoliidae, order Illiciales) and Dilleniaceae.The leaves of Dilleniaceae are simple, alternate, without stipules, or winged and adnate to the petiole. The blade is serrate, leathery and shows several pairs of conspicuous secondary nerves. The flowers are yellow or white, perfect, hypogynous and showy. The calyx comprises of 3–20 spoonshaped, deciduous and fleshy sepals originating in a centrifugal sequence and the corolla comprises of 2–5 very thin petals which are often crumpled in buds. The andrecium comprises of 5–20 stamens originating in centrifugal sequence. The gynecium consists of a single to 20 carpels arranged in a single whorl more or less united to form a compound ovary with distinct styles. The fruits are variable and the seeds are embedded in a juicy and showy aril. Pharmaceutical interest: A classical example OH of Dilleniaceae is Dillenia suffruticosa (Griff.) OH Martelli (shrubby Dillenia), an invasive species native to Southeast Asia, which is widely HO O OH grown as an ornamental shrub in tropical countries for its yellow flowers and red fruits. Not much is really known yet about the pharmaOH O cological potential of this family and it will be interesting to learn whether more intensive Myricetin future research on this family will disclose any molecules of therapeutic interest. Note that betulinic acid is known to occur in this family. About 20 species of Dilleniaceae are used for medicinal purposes in the Asia-Pacific. These are often used to treat fever and cough, stop diarrhea, promote urination, and to wash hair and infected skin, mostly on account of the saponins and tannins. Acrotrema costatum Jack [From Greek, akros = highest, and trema = aperture and from Latin, costatus = ribbed] Physical characteristic: It is a brightly colored, medium-sized, rainforest herb of Malaysia, which develops from woody underground stems. Leaves: in rosette, simple, 12 cm–30 cm × 6 cm–12 cm, hairy, obovate, serrate, deep green, ribbed and penciled with red. The flowering stems stand up to a height of 10 cm and are covered with long reddish hair.

Common name: Yellow jungle star. Uses: In Malaysia, Acrotrema costatum Jack is used to invigorate health after childbirth. Not much is known about the therapeutic potential of Acrotrema costatum Jack.

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The inflorescences hold 8–10 bright yellow flowers. The flowers comprise of 5 red and hairy sepals, 5 yellow, showy, deciduous and very thin petals, stamens organized in 3 bundles and a gynecium consisting of 3 pistils. The fruits are 3 follicles, irregularly dehiscent (Fig. 80). Warning: Caution must be taken as the toxic effects of this plant are unknown. Fig. 80. Acrotrema costatum Jack.

Dillenia excelsa (Jack) Gilg [After J J Dillenius (1684–1747), a German botanist; and from Latin, celsus = lofty] Synonymy: Wormia excelsa Jack, Wormia tomentella Mart. Common names: Simpoh ungu (Malay). Uses: In Indonesia, the leaves are applied to the head to treat fever and to assuage headache. The therapeutic potential of Dillenia excelsa (Jack) Gilg is unexplored til to date.

Physical description: It is a tree which grows wild to a height of 15 m and a girth of 60 cm. It is found in the rainforests of Malaysia and Indonesia. The stems are terete, smooth and glabrous. Leaves: simple, spiral and without stipules. The petiole is 3 cm– 3.3 cm long, thin and deeply channeled. The blade is 26 cm × 15.3 cm– 11.5 cm × 16 cm, acute both at the base and at the apex, and has a margin that is laxly serrate. The blade

Fig. 81. Dillenia excelsa (Jack) Gilg. From: KLU Herbarium 006688. Flora of Malaya. Field collector: Benjamin C Stone, 13 Nov 1966. Geographical localization: Templer Park, Kanching, Malaysia, altitude: 750 ft. Botanical Identification: 10 Oct 1969, KM Kochummen.

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shows about 15 pairs of secondary nerves which are prominently raised above and below. The tertiary nerves are raised below the blade. The inflorescences are terminal cymes of fragrant flowers which are globose in buds, 1.5 cm in diameter and velvety. The calyx comprises of 5 ovate, 1 cm–2 cm × 9 mm– 1 cm sepals which are velvety on the outside. The corolla consists of 5 petals which are very thin, nerved, yellow, measuring 4 cm × 2.5 cm. The stamens are numerous, linear and light mauve and the anthers are 7 mm long. The gynecium consists of 4, 1.5 cm × 5 mm, light mauve and free carpels (Fig. 81). Warning: Caution must be taken as the toxic effects of this plant are unknown. Dillenia indica L. [After J J Dillenius (1684–1747), a German botanist; and from Latin, indica = from India]

Synonymy: Dillenia speciosa Thunb. Common names: Elephant apple tree, simpoh, chimpu (Malay).

Physical description: It is a magnificent tropical tree which grows to a height of 12 m, in the geographical zone spanning India to South China and Indonesia. The tree is truly magnificent and often grown for ornamental reasons. The bark is reddish and the stems are hairy. Leaves: simple, dark green, 20 cm–30 cm × 7 cm–10 cm, leathery, lanceolate to ovate-lanceolate, serrate, pubescent underneath and strongly ribbed with up to 40 pairs of secondary nerves. The flowers are 15 cm–20 cm, pure white, showy, and axillary on a stout 9 cm long pedicel. The sepals are orbicular, green, very succulent and persistent in fruits. The petals are pure white, obovate, oblong, deciduous and very thin. The andrecium consists of numerous reddish stamens. The gynecium comprises of 20 carpels. The fruits are edible, globose, 15 cm in diameter, green, very heavy, succulent and contain several heavy seeds (Fig. 82).

Fig. 82. Dillenia indica L.

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Uses: In Burma, the bark, fruits or leaves of Dillenia indica L. are used to combat fever. In Malaysia, the pulp of the fruit is used to manufacture shampoo.

O O O Dillenic acid D

Pharmaceutical interest: One might set the hypothesis that the fruit of Dillenia indica L. is used to wash hair on account of contains probably saponins. Saponins irritate the skin and are seldom used in cosmetics, but these are however safer than the present sulphated hydrocarbons which are known to be carcinogenic.The pharmacological potential of Dillenia indica L. is still awaiting experimental assessment. Note that dillenic acids A, B, C and D are oleanenes triterpenoids characterized from Dillenia papuana, which inhibit the growth of Bacillus subtilis, Escherichia coli, and Micrococcus luteus cultured in vitro (Nick et al., 1994, 1995). (Antioxidant activity of the extracts of fruits are antioxidant, Food Chem 90 (4): 2005, 891–896, MdH Abdille, RP Singh, GK Jayaprakasha and BS Jena.) References Nick, et al. (1994) J Nat Prod 57(9): 1245–1250. Nick, et al. (1995) Phytochem 40(6): 1691–1695.

Warning: Caution must be taken as the toxic effects of this plant are unknown. Tetracera indica (Houtt. ex Christm. & Panz.) Merr. [From Greek, tettares = four, keras = horn and from Latin, Indica = from India] Physical description: It is a large Synonymy: Assa indica Houtt. ex woody rainforest climber found in Christm. & Panz., Tetracera assa DC. Malaysia and Indonesia. Leaves: Common names: Akar mempelas, simple and alternate. The blade is mempelas, mempelas minyak (Malay). broadest near the apex, round or acuminate, usually lobed near the tip, and very rough to the touch. The inflorescences are very large, branched and spreading. The flower pedicels are 1.5 cm long. The flowers are white, fragrant and small. The calyx consists of 5 pink sepals. The corolla consists of 5 petals which are white and membranaceous. The andrecium consists of several pink

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anthers. The gynecium is made of 2– 4 ovaries which are distinct, smooth, glossy and ripening red (Fig. 83). Uses: In Malaysia, a powder of Tetracera indica (Houtt. ex Christm. & Panz.) Merr. is used to soothe inflamed areas. In Indonesia, the sap is ingested to relieve cough and a paste made from the leaves is applied to poisonous bites.

Pharmaceutical interest: The pharmacological potential of Tetracera indica (Houtt. ex Christm. & Panz.) Merr. is unexplored til to date. Note that betulinic acid, 3-cis-p-coumaroyl maslinic acid, and 3-trans-p-coumaroyl Fig. 83. Tetracera indica (Houtt. ex Christm. & maslinic acid characterized from Panz.) Merr. Tetracera boiviniana inhibit the enzymatic activity of DNA polymerase with IC50 values of 14 µM, 15 µM, and 4.2 µM in the presence of bovine serum albumin and 6.5 µM, 7.5 µM, and 2.0 µM without bovine serum albumin respectively, and enhance the effects of bleomycin in cultured P-388D1 cells (Ma J et al., 1999).

H

R2

H R1 H Betulinic acid (R1= β OH, R2= COOH)

Reference Ma J, et al. (1999) J Nat Prod 62(12): 1660–1663.

Warning: Caution must be taken as the toxic effects of this plant are unknown.

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B. Order THEALES Lindley 1833 The order Theales consists of 18 families and about 3500 species of trees, shrubs, climbers and herbs, which are thought to have originated from the order Dilleniales (Appendix I). Theales have attracted a great deal of interest on account of their ability to elaborate a series of cytotoxic, antimicrobial and neuroactive phenolic substances. This order is a common ancestor for two major groups: one comprising Malvales, Lecythidales, Capparales, Violales and Nepenthales, and another group which includes Ericales, Ebenales and Primulales.

1. Family DIPTEROCARPACEAE Blume 1825 nom. conserv., the Meranti Family Physical description: The family Dipterocarpaceae consists of about 16 genera and nearly 600 species of tropical timber trees, some of which are the tallest of all Magnoliopsida, commonly accumulating resins (triterpenes and sesquiterpenes), tannins, proanthocyanidins and ellagic acid. The wood of Dipterocarpaceae is extremely hard and dense, and is of excellent quality. The leaves in this family are simple, stipulate, alternate, particularly thick and quite hard. The flowers are perfect and regular, and arranged in an axillary raceme or panicles. The calyx comprises of 5 imbricate sepals, and the corolla comprises of 5, distinct or connate, convolute in bud and spirally twisted petals. The andrecium consists of 10 trunks of bundles, 5–several, and is initiated in centrifugal sequence. The gynecium comprises of 2–5 carpels forming a compound, plurilocular ovary with axillary placentation. The fruits are dry, woody and quite often winged with the persistent sepals. Pharmaceutical interest: Belonging to the family Dipterocarpaceae are several very valuable timber trees such as Shorea robusta Gaertn. (Saul tree). Dipterocarpaceae often produce resins: Vateria indica L. (piny resin, Indian copal, white dammar), Dryobalanops aromatica Gaertn. (Sumatra camphor tree), Dipterocarpus turbinatus Gaertn. (gurjun basalm, garjan or kanyin oil) and Dipterocarpus tuberculatus Roxb. (eng oil). The resin obtained from Vateria indica L., is used to make ointments, stop flatulence, treat bronchitis and piles, heal boils and to invigorate health. The resins (gurjun) obtained from

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a number of species of plants classified within the genera Dipterocarpus are fixatives in perfumery and are used to prepare guaiazulene. Dammar (British Pharmaceutical Codex, 1923) OH consists of the resins obtained from trees classified within the genus Shorea, Hopea, and Balanocarpus. Dammar is used to make varnishes, a mounting agent in microscopy and HO plaster masses. The nuts of Shorea macroOH phylla contain an edible fat, which can be used Resveratrol instead of cocoa butter in the manufacture of chocolates. In China, an oil obtained from the seeds of Dipterocarpus lamellatus was used to treat leprosy. There is an expanding body of evidence to suggest that oligomers of resveratrol and oligostilbenes of Dipterocarpaceae are remarkably cytotoxic and it will be interesting to learn whether more intensive future research on dipterocarps will disclose any molecules of chemotherapeutic interest. In Southeast Asia, about 20 Dipterocarpaceae plant species are medicinal. Note that the resins of dipterocarps are often used to heal wounds. Dipterocarpus alatus Roxb. [From Greek, dis = two, pteron = wing, karpos = fruit and from Latin, alatus = having wings] Synonymy: Dipterocarpus incanus Roxb., Dipterocarpus gonopterus Turcz. Common names: Kanyin (Burmese); yang khao (Thai); chhoeuteal trach (Cambodian); chhoeu teal thom (Laos, Vietnamese).

Physical description: It is a resinous timber which grows to a height of 45 m and a girth of 4 m. It is found in the lowland tropical rainforest of Burma, Cambodia, Thailand, Malaysia, Laos and Vietnam.The bark is pale grey and the bole of 1 m diameter. Leaves: simple, alternate and stipulate. The stipules are 5 cm–9 cm long and covered with stellate hairs. The petiole is stout, 3.9 cm–2.5 cm long, woody, obscurely

Uses: The resin of Dipterocarpus alatus Roxb. is used externally to heal wounds and to counteract putrefaction in several Southeast Asian countries. In Cambodia, the bark is used to invigorate health, expel impurities, and to treat rheumatism and liver complaints, while the resin is used to heal ulcerated wounds. In India, the resin is used to treat gonorrhea. In Cambodia, Laos, and Vietnam, the resin is used to heal ulcerous sores and to treat blenorrhagia. In Thailand, the bark is used to invigorate health and to mitigate toothache, while the resin is used to heal the wounds of cattle. The resin is used for varnishing. To date, the pharmacological potential of Dipterocarpus alatus Roxb. is unexplored.

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flattened above, knee-shaped and cracked transversally near the base of the blade. The blade is ovate, thick, 10 cm×20 cm–5.7 cm×11.3 cm, glabrous on the surface and shows a few stellate hairs below. The apex of the blade is acute, the margin is wavy and recurved, and the blade shows 12–18 pairs of secondary nerves. The tertiary nerves are scalariform, visible from below, and obscure above. The flowers are arranged in axillary 3– 7 flowered spikes. The calyx is tubular and 1 cm–1.5 cm long. The petals are 3 cm long and pubescent outside. Fig. 84. Dipterocarpus alatus Roxb. From: KLU Herbarium 12598. Plants of CamboThe andrecium comprises of 30–32 dia. Field collector.: Benjamin C Stone, 21 Mar stamens with flattened, 3.8 mm long 1970. Geographical localization: Siem Reap, filaments and 4.5 mm long anthers, along route to Angkor Wat, Cambodia. Botanithe connectives of which produce a cal Identification: Ashton 14 Feb 1973. bristle of 3 mm–8 mm in length. The ovary is densely tomentose and the style 10 mm long. The fruits are 5winged and somewhat bluish 2.5 cm– 2.8 cm nuts with a pair of oblong, 12.5 cm × 2.6 cm–11 cm × 1.8 cm, hard, somewhat glaucous and 3–nerved wings (Fig. 84). Warning: Caution must be taken as the toxic effects of this plant are unknown. Dipterocarpus intricatus Dyer [From Greek, dis = two, pteron = wing, karpos = fruit; and from Latin, tricare = tricks] Physical description: It is a magnificent, heavily fruiting, small resinous tree which grows to height of 9 m and a girth of 22 cm. It is abundant in Cambodia and Thailand in degraded or semi-cultivated grounds. Leaves: simple and spiral. The petiole, inflorescences, young stems and leaves are characteristically woolly. The petiole is

Common name: Krat (Thai); trach (Cambodia); dau ˆ long (Vietnamese). Uses: In Cambodia, the bark of Dipterocarpus intricatus Dyer is used to treat rheumatism, but this property has not yet been confirmed experimentally.

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1.5 cm–2.6 cm long. The blade is leathery, ovate, acute–round at apex, obscurely cordate at the base and the margin is slightly wavy. The blade shows a midrib that is raised above and sunken below, and 16–18 pairs of secondary nerves obscurely sunken above and raised below, as well as scalariform tertiary nerves. The inflorescences are axillary panicles. The fruits are 1 cm × 1.7 cm– 1.5 cm x 1.4 cm nuts which are magenta, intricate and bearing a pair of 7.8 cm–10 cm × 2 cm–1.7 cm, singlenerved and oblong wings formed by Fig. 85. Dipterocarpus intricatus Dyer. persistent sepals (Fig. 85). Warning: Caution must be taken as the toxic effects of this plant are unknown.

From: KLU Herbarium 12593. Plants of Cambodia. Geographical localization: 5 Km from Banteay Srei, nr. Angkor. Field collector: Benjamin C Stone, 21 Mar 1970. Botanical identification: Ashton 15 Feb 1973.

Dipterocarpus obtusifolius Miq. [From Greek, dis = two, pteron = wing, karpos = fruit, from Latin, obtundere = obtuse and folium = leaf] Physical description: It is a resinous timber which grows to a height of 15 m and a girth of 80 cm. It is common on the mountain ridges in the Synonymy: Dipterocarpus punctulatus Pierre, Dipterocarpus vestitus Wallich ex Dyer Common names: Hiang (Thai). Uses: In Cambodia, Laos and Vietnam: the resin is used to mitigate abdominal discomfort. To date, the pharmacological potential of this plant is unexplored.

Fig. 86. Dipterocarpus obtusifolius Miq. From: KLU Herbarium 19004. The Forest Herbarium (BKF), Royal Forest Department. Flora of Thailand. Field collector & botanical identification: C. Chaloenphol, 12 Apr 1971. Geographical localization: Chaiyaphum, Thailand.

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tropical rainforest of Thailand, Cambodia, Laos and Vietnam. The stems and petioles are woolly. Leaves: simple and spiral. The petiole is 3.5 cm–5.5 cm × 3 mm–4 mm.The blade is ovate, leathery, 14.7 cm× 9.7 cm–21.5 cm×13.9 cm, acute at the apex and obscurely cordate at the base and wavy at the margin. The blade shows a midrib and 10–13 pairs of secondary nerves raised below and sunken above. Internerves are noticeable. The fruits are globose, smooth green nuts, measuring 2 cm–1.7 cm in diameter, with a pair of 1.5 cm–8.5 cm× 2.6 cm–2 cm, reddish and 3-nerved wings (Fig. 86). Warning: Caution must be taken as the toxic effects of this plant are unknown. Dryobalanops aromatica Gaertn. [From Greek, drys = oak, balanos = nut, and aromatikos = aroma] Physical description: It is large timber tree which is recognized miles away by its greyish looking foliage and the shape of its crown, which is best described as being like an umbrella. It is found in primary rainforests up to 800 feet above sea level, in Malaysia and Indonesia. This tree grows to a height of 50 m. Leaves: simple, spiral, up to 10 cm long, leathery, ovate and acuminate.The inflorescences consist of terminal 5 cm long panicles of white and fragrant flowers. The sepals are lanceolate acute, 7.5 mm long and scurfy. The petals are thin, lanceolate, acute, white, and as long as the sepals. The andrecium consists of 35–45 stamens, with short filaments and long narrow beaked anthers. The fruits are oblong, conic, and 2.5 cm long nuts, the sepals forming 8 cm long, obtuse, thick and reddish wings (Fig. 87). The method of extracting camphor or isi kapur is to split the bark and pick the crystals out of the small cavities. Malays and Indonesians believe that

Synonymy: Dryobalanops camphora Colebr. Common names: Malay camphor, Borneo camphor; kapur barus, kapur, kayu kapur (Malay); apakva (Sanskrit).

Fig. 87. Dryobalanops aromatica Gaertn.

Subclass Dilleniidae

the man who should collect the camphor should speak in a very respectful language, known only to old folks. Oil of camphor known to the Malays by the name of minyah kapur is obtained by making a small cut penetrating into the wood about 10 cm. The resin of Dryobalanops aromatica Gaertn. consists of borneol, camphor, terpineol and other terpenes.The wood contains among other things, dipterocarpol, βsitosterol, and dryobalanone. Borneol and camphor are known to be responsible for contact dermatitis. Pharmaceutical interest: Note that borneol of Dryobalanops aromatica inhibits the nicotinic receptor agonist 1,1-dimethyl-4-phenylpiperazimium iodide-induced secretion of [3 H] norepinephrine by bovine adrenal chromaffin cells with an IC50 of 70+/-12 µM in a non–competitive way (Oh KS et al., 2000; 2001, Park TJ et al., 2003).

OH

143

Uses: The camphor of Dryobalanops aromatica Gaertn. was known from very early times. It is from the Malay word kapur that the word camphor is derived. This camphor was the only kind known in Europe in the Middle Ages and was the καϕoυρα of the later Greek physicians, who obtained knowledge of it through the Arab traders. It has been mentioned in a number of Arabian poems of the 6th century, and Marco Polo described it as being superior to any other and worth its weight in gold. In 1851, the price of this camphor in Borneo was 3 dollars a catty (95 shillings a pound), and in Canton 8 shillings a pound. Imported into China from very early times, it was valued for its ability to invigorate health, produce venereal desire, reduce inflammation and body temperature, stimulate appetite, and to aid the physiological pathways of the body. In Malaysia, the powdered oleoresin is used to heal wounds. Indonesians use the kernel of the fruit to assuage pain and to check bleeding. In Asia, camphor is used at funerals and magic ceremonies.

Borneol

References Oh KS, et al. (2000) Pharmacol Res 42(6): 559–564. Park TJ, et al. (2003) Biochem Pharmacol 65(1): 83–90.

Warning: Camphor is irritating to the skin and causes keratitis. Large doses of it induce nausea, diarrhea and vomiting, dizziness, tension, hallucinations and mental confusion. The initial stimulation is followed by central nervous system depression which may involve seizures, coma or death due to respiratory failure.

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Hopea odorata Roxb. [From Latin, odorem = odor] Physical description: It is a resinous Common names: Merawan siput timber tree which grows to a height of jantah, cengal pasir, cengal mas 45 m and a girth of 1.20 m. This tree is (Malay), thengan (Burma), koki found in the lowland tropical forests of (Cambodia); sao den (Vietnam); koki, Cambodia, Laos, Vietnam, Malaysia, mosau, thmar (Cambodia); kh’e:n Burma and Thailand, in deep, rich soils (Laos); takhianthong, takhian-yai up to 300 m altitude and rarely far away (Thailand). from streams. The stems are smooth, terete and velvety when young. Leaves: simple and alternate. The petiole is 7 mm–1 cm long and somewhat curved, and velvety when young. The blade is ovate-lanceolate, leathery, 10 cm–20 cm long, slightly unequal at the base, and acute-acuminate at the apex. The margin is slightly wavy. The blade shows a midrib which is flat above, raised below and grooved. It has 9–12 pairs of indistinct secondary nerves, and scalariform tertiary nerves. Tufts of hairs can be observed at the axis made of secondary nerves and a midrib. The inflorescences consist of 15 cm long velvety axillary panicles. The female flowers are very small and velvety, and comprise of 5 pinkish petals, which are hairy on both sides, and an ovary gradually narrowed into a conical stylopodium and a long cylindrical style. The fruits are globose nuts of about 1 cm in diameter and bearing a pair of 2 long wings at the apex (Fig. 88). Uses: In Burma, the resin of Hopea odorata Roxb. is used to check bleeding. In Cambodia, Laos, Cambodia, and Vietnam, the bark is used to treat gingivitis, toothache and incontinence. In Malaysia, the resin is used to heal wounds and sores.

Pharmaceutical interest: A butanolic extract of Hopea odorata Roxb. inhibits the proliferation of human hepatocellular carcinoma cells (Hep G2) cultured in vitro with an IC50 value of 20.14 µg/mL (Norizah A et al., 2000). Phenolic substances are most probably responsible for this activity, which has however to be further confirmed. Is resveratrol involved here?

Fig. 88. Hopea odorata Roxb. From: KLU Herbarium 19038. Flora of Thailand. The Forest Herbarium (BKF), Royal Forest Department. Field collector & botanical identification: S. Phusomsaeng. 10 Apr 1971. Geographical localization: Pen; Trang Khao Chong, South Thailand.

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Reference Norizah A, et al. (2000), 10th Annual Scientific Meeting of the Malaysian Association of Clinical Biochemists, 14–15 August, Kuala Lumpur.

Warning: Caution must be taken as the toxic effects of this plant are unknown. Shorea sumatrana (van. Sl. Ex Foxw) Sym. [Shorea after Sir John Shore (17511834), Governor General of India (1793–1798); and Latin sumatrana = from Sumatra] Physical description: It is a timber which grows to a height of 36 m and a girth of 2.5 m in the rainforest of Malaysia and Indonesia. The stem is smooth and glabrous, except for the young ones which are covered with a few stellate hairs. Leaves: simple, alternate and stipulate. The stipules are 4 mm × 2 mm, triangular, caducous and velvety, and the petiole is slightly channeled, glabrous, 1 cm–1.6 cm long, cracked transversally near the blade. The blade is hard, oblong-elliptic, leathery, heavy, and glabrous. The base is round and the apex acute. The margin is slightly wavy and recurved. The midrib and secondary nerves are sunken above the blade and raised beneath. The midrib is slightly channeled below and there are 9–10 pairs of secondary nerves. The tertiary nerves are hardly visible. The inflorescences consist of terminal or axillary panicles of 8 cm– 10 cm long, covered with a few stellate hairs. Flower: the calyx is very small, velvety and comprises of 5 sepals of unequal size (1 mm–3 mm long). The corolla comprises of 5 petals which are reddish-yellow, linear,

Synonymy: Isoptera borneensis King non R. Scheffer ex Burck, Isoptera sumatrana v. Slooten ex Thorenaar. Common names: Sengkawang ayer (Malay).

Fig. 89. Shorea sumatrana (van. Sl. Ex Foxw) Sym. From: KLU Herbarium 65301. Field collector: x. m. x., 17 Sep 1955. Geographical localization: Slong, Ulu Kelantan, near a stream, altitude 100 feet, Northeast Malaysia. Botanical identification: 14 Oct 1955, x.m.x. From KLU Herbarium 001517. Field collector: Mohd. Kasim Bin Rajab. Geographical localization: Kepong, F.R.I., Selangor. Roadside in front of nursery, 12 Jun 1963, West Malaysia. Botanical identification: Mohd. Kasim Bin Rajab & Ashton, 12 Feb 1973.

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1.4 cm × 5 mm–1 mm, hairy below and contorted in buds. The fruits are glaucous, velvety and slightly acuminate 1.4 cm × 1.1 cm nuts surrounded by 5 round, woody, irregularly shaped, 5 mm–1 cm×1 cm–7 mm persistent sepals (Fig. 89). Pharmaceutical potential: To date, Uses: In Indonesia, an oil expressed the pharmacological potential of Shorea from the seeds is used externally to sumatrana (van. Sl. Ex Foxw) Sym. is heal wounds and sores in the mouth. still unknown and it will be interesting to learn whether more intensive future research of this plant will disclose any molecules of chemotherapeutic interest. Warning: Caution must be taken as the toxic effects of this plant are unknown.

2. Family THEACEAE D.Don 1825 nom. conserv., the Tea Family Physical description: The family Theaceae consists of 40 genera and 600 species of tropical and sub-tropical shrubs and trees commonly producing tannins, proanthocyanins, ellagic acid, saponins, caffeine and xanthones. It is generally agreed that the family Theaceae is closely related to the family Dilleniaceae, except for the compound ovary and seeds that lack aril. The leaves are simple, alternate, crenate and without stipules. The flowers are showy, axillary, solitary, perfect and hypogynous, and comprise of 5 imbricate and free sepals, and 5 or more, free, imbricate, often white petals.The andrecium comprises of numerous stamens developing centrifugally with tetrasporangiate and dithecal anthers opening by longitudinal slits. The gynecium consists of 3–5 carpels united into a compound, 3–5 locular ovary with axillary placentation. The fruits are dehiscent capsules. Pharmaceutical interest: Classical examples of Theaceae are Camellia sinensis (L.) Kuntze. (Tea) and Camellia japonica L. (Camellia). In Southeast Asia, about 15 species of Theaceae are used for medicinal purposes, notably to stop hemorrhages and dysentery, and to treat skin diseases on account of their astringent properties.It will be interesting to learn whether more intensive future research on the phenolic compounds of this family will disclose any molecules of therapeutic interest.

O N

N O

N Caffeine

N

Subclass Dilleniidae

147

Camellia sinensis (L.) O. Ktze. [After Kamel, 17th century Jesuit and botanist and from Latin, sinensis = from China] Physical description: It is a shrub Synonymy: Thea sinensis L., Thea native to Asia and has been culticochinchinensis Lour., Thea vated for ages in China and Japan. chinensis Sims The bark is dark grey and the stems Common names: Tea; the´ (French); glabrous and terete. Leaves: simple, spiletpet (Burmese); ming (Chinese); ral and without stipules. The petiole is caolo (Vietnamese); cha 4 mm–7 mm × 4 mm, channeled above, (Portuguese); teylai (Tamil). hairy and rugose. The blade is elliptic, rigid, 11 cm × 5 cm–12.5 cm × 5 cm. The margin is recurved and serrulate, and the blade shows 9–11 pairs of secondary nerves. The flowers are showy and axillary. The calyx consists of 5 sepals which are round, hard, 4 mm–5 mm in diameter, and finely ciliate. The corolla consists of 5 thin petals which are white, obovate, 1 cm×1.2 cm, and somewhat pubescent beneath.The stamens are numerous and showy. The ovary is villous and develops 3 glabrous styles connected beyond the middle. The fruits are capsular, 3-lobed or irregularly shaped, glossy and green at first, dehiscent, and approximately 3 cm–4 cm in diameter. The seeds are smooth, brownish, globose and of 1.8 cm in diameter (Fig. 90).

Tea spread to Europe during the 17th century. In Occident, the most popular form of tea is black tea, prepared by drying, rolling and crushing fresh young leaves kept in a damp area to promote oxidation. Green teas are non-oxidized and are enjoyed in the Orient.

Fig. 90. Camellia sinensis (L.) Kuntze.

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Pharmaceutical potential: The tonic Uses: In Asia, an infusion of the property of Camellia sinensis (L.) leaves is used to make a drink (tea) Kuntze is mediated by caffeine, a purine to invigorate the mind and the heart, alkaloid, which stimulates the cerestop spasms and dysentery, treat bral cortex and has inotropic positive, fever cough, and nervous disorders, and to promote urination and relaxes the vessels and promote urinadigestion. In Europe, tea has been tion. A growing body of evidence indilisted in the 1949 edition of the British cates that flavans of Camellia sinensis Pharmaceutical Codex and is found (L.) Kuntze are of possible therapeutic in the 10th edition of the French interest. Pharmacopoeia. Stuart reports the Chemotherapeutic properties: One Pen Ts’ao Kang Mu as “tea clears such compound is (−)-epigallocatechin- the voice, gives brilliancy to the eyes, 3-O-gallate abrogates the survival of invigorates the constitution, improves the mental faculties, opens up the xenograft tumors (Sintippour MR et al., avenues of the body, promotes 2001). Catechins of tea are bacteridigestion, removes flatulence, and cidal towards Streptococcus mutans regulates the body temperature”. and Streptococcus sobrinus which are (Stuart GA, 1911). responsible for dental caries (HamiltonMiller JMT et al., 2001). Anti-oxidant properties: Note also that the relative risk of incident myocardial infarction is lower in tea-drinkers (Geleijnse JM et al., 2002) and tea lowers cholesterolaemia in animal models (Bursill C et al., 2001). Black tea has antiinflammatory properties (Chaudhuri AK et al., 2005). OH OH HO

O

OH O O

OH OH HO

OH

( - ) - Epigallocatechin - 3 - O - gallate

References Bursill C, et al. (2001) J Agr Food Chem 49(11): 5639–5645. Chaudhuri AK, et al. (2005) Pharmacological Research 51(2): 169–175. Geleijnse JM, et al. (2002) AM J Clin Nutr 75(5): 880–886. Hamilton-Miller JMT, et al. (2001) J Med Microbiol 50(4): 299–302. Sintippour MR, et al. (2001) Nutr Cancer 40(2): 142–150.

Subclass Dilleniidae

149

Warning: There is an expanding body of evidence to suggest that condensed catechin combined with smoking causes esophageal cancer.This effect apparently may be overcome by adding milk which binds to tannin preventing its deleterious effects. Note that tea is diuretic and contributes to dehydration.

3. Family CLUSIACEAE Lindley 1826 nom. conserv., the Mangosteen Family Physical description: The family Clusiaceae, or Guttiferae, consists of 50 genera and 1200 species of tropical plants which are thought to have originated from the family Theaceae. These are trees, climbers or herbs, exuding a sticky yellow gum resin and often contain proanthocyanidins, tannins, and various sorts of phenolic substances including xanthones. The leaves are simple, without stipules, decussate or whorled, principally entire, and often showing long, thin and parallel secondary nerves. The petiole is often clasping and small. The flowers are often showy, fragrant, unisexual, regular and hypogynous, joined together in terminal and cymose inflorescences, or less often solitary and terminal. The sepals are free and overlapping, and there are 2–14 free, imbricate or convolute overlapping petals. The andrecium consists of limited trunk-bundles of stamens initiated in a centrifugal sequence, and the anthers open by longitudinal slits. The gynecium comprises of 1 to several carpels forming a compound superior ovary with axillary placentation, including as many locules as carpels and a single style. The stigma is big, lobed or peltate. The fruits are berries, drupes or nuts, and the seeds are often oily. Pharmaceutical interest: Classical examples of Clusiaceae are Garcinia mangostana L. (mangosteen fruit tree), Mammea americana L. (mammee-apple), Pentadesma butyracea Sabine (butter or tallow tree), Garcinia kola Heckle (bitter kola), Garcinia morella, Calophyllum inophyllum L. (Alexandrian laurel, Indian poon), Mesua ferrea (iron wood) and Ascyrum hypericoides (St. Andrew’s cross). The yellow gum resin of Garcinia hanburyi Hook. f. (gamboges tree) was used (gamboje, British Pharmaceutical Codex, 1934) to relieve the bowels of costiveness (dose: 30 mg–60 mg). The solid fat expressed from the seeds of Garcinia indica (Thouars) Choisy or kokum butter (Indian Pharmacopoeia) has been used to make suppositories. The flowering tops of Hypericum perforatum L. (St. John’s Wort) has been used to promote urination (Hypericum, Russian Pharmacopoeia, 1961, tincture prepared by

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percolation with alcohol 40%). Most of the medicinal Clusiaceae have healing properties. The flowering tops Hypericum perforatum L. (St. John’s Wort) although photosensitizing, are used to treat depression, and to heal wounds. In Ceylon, the oil of Calophyllum calaba L. is a remedy for irritated skin. The gum-resins of Caraipa fasciculata (Brazil) and Clusia flava Jacq. (West Indies) are used to heal wounds. Of recent interest in this family are a series of neoflavonoids, prenylated xanthones, dipyranocoumarins, and quinones, which display experimentally monoamine oxidase (of MAO A and to a lesser extent of MAO B), antifungal, antibacterial, anti-platelet aggregation, anti-inflammatory and antiHuman Immunodeficiency Virus activities. Hypericin and calanolides characterized from the Hypericum species and Calophyllum species respectively, are undergoing clinical trials as anti-Human Immunodeficiency Virus drugs. The therapeutic development of natural products characterized from the family Clusiaceae would not be surprising. In Southeast Asia, about 50 species of plants classified within the family Clusiaceae are used for medicinal purposes. The resin is often used to treat skin diseases and to heal wounds whereas the bark is astringent. Calophyllum inophyllum L. [From Greek, kalos = beautiful and phullon = leaf] Physical description: It is a magnifiSynonymy: Calophyllum bitangor cent coastal, large tree which grows wild Roxb. in the geographical zone spanning India Common names: Alexandrian to Fiji. It is often cultivated to decorate laurel, Indian poon, sweet-scented parks and roadsides. The bark is grey Calophyllum; calophylle faux to fawn, with wide, shallow, markedly tacamahac (French); bintangor laut boat-shaped fissures and exudes a clear (Malay). golden yellow sticky gum-resin. Leaves: simple, without stipules and decussate. The blade is broadly elliptic-oblong, large (8 cm–16 cm × 4 cm–8cm), rigid, glossy, and leathery. The apex is round or notched, the base tapered, and there are numerous, distinct, parallel and straight secondary nerves. The inflorescences are long (7 cm–8 cm) and axillary laxly flowered raceme. The flowers are delicate, showy (1 cm), and supported by long, thin (3 cm) and white pedicels.The 4 sepals and petals are whitish, ripening to brown, and are deciduous. The stamens are numerous and yellowish-red, inserted at the base of an ovoid, pinkish and superior ovary developing upward into a long and thin style. The fruits are globose, large, 2 cm in diameter, green drupes (Fig. 91).

Subclass Dilleniidae

151

Uses: From the seeds of Calophyllum inophyllum L. is expressed the dilo oil, which is used to heal wounds and treat ringworms and infected skin. In Indonesia, the gum-resin is used make plasters. It is burned as incense, and is used to remove tumors. The bark is applied to swollen parts and is used to promote urination, remove blood from urine and treat gonorrhea. A maceration of leaves is applied to the inflamed eyes. In the Philippines, the juice expressed from the leaves is used to heal hemorrhoids. In Cambodia, Laos, and Vietnam, the gum resin is used to heal ulcers and infected wounds. In India, the oil expressed from the seeds is used to soothe inflamed parts and exanthaematous eruptions.

Pharmaceutical interest: Anti-HIV property: In regard to the antiviral property of Calophyllum species, a Fig. 91. Calophyllum inophyllum L. number of experiments conducted both in vitro and in vivo have clearly demonstrated that dipyranocoumarins are able to inhibit the enzymatic activity of the Human Immunodeficiency Virus type-1 reverse-transcriptase. Calanolides A and B characterized from Calophyllum lanigerum inhibit Human Immunodeficiency Virus type-1 reversetranscriptase as well as the replication and the cytopathicity of the Human Immunodeficiency Virus type-1 with respective EC50 values of 0.1 µM and 0.4 µM (Kashman Y et al., 1992). From Calophyllum inophyllum L., costatolide, inophyllum P, and inophyllum B inhibit the replication of the Human Immunodeficiency Virus (Patil AD et al., 1993; Spino C et al., 1998). Reverse-transcriptase is a key enzyme in the life-cycle of the Human Immunodeficiency Virus and Retrovirus in general. Once the O Human Immunodeficiency Virus binds to the CD4 surface glycoprotein of a lymphocyte, the viral envelope fuses with the cytoplasmic membrane of the lymphocyte and the viral RNA is internalized into the lymphoO O O cyte where it starts to replicate. OH

The transcription of the viral RNA into DNA is set into motion by a viral reverse-transcriptase, which is a

Calanolide A

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Division MAGNOLIOPHYTA

heterodimer consisting of 61 KDa and 52 KDa subunits. The viral DNA synthesized is then integrated into the genome of the lymphocyte in a process dependent on a viral endonuclease. When the portion of viral DNA is activated, the genetic machinery of the host-cell is then used to replicate several new viruses which finally kill the cell. Reverse-transcriptase inhibitors have attracted a great deal of interest on account of their ability to treat Human Immunodeficiency Virus infection. One such compound is zidovudine (AZT® ), which is a close structural analogue of thymidine, from which it differs by a 3-azido group instead of a 3 -hydroxyl group.

Fig. 92. Calanolide inhibits the enzymatic activity of reverse-transcriptase (R) and as a result the synthesis of the DNA (DNA v) from the RNA (RNA v) of the human immunodeficiency virus is abrogated. Capside (C), DNA of the host-cell (DNAc).

Another example is zalcitabine (ddC® ), which is a close structural analogue of deoxycitidine, containing a hydrogen atom on the 3 carbon instead of a hydroxyl group. After phosphorylation, zidovudine is incorporated into the growing DNA chain via viral reverse-transcriptase. The absence of hydroxyl group on the 3 carbon causes chain termination and therefore inhibition of reversetranscriptase (Fig. 92). Other properties: A series of 4-phenylcoumarins, including calocoumarin A, inhibit the early expression by Raji cells of Epstein-Barr Virus (EBV) antigen induced by 12-O-tetradecanoylphorbol-13-acetate (TPA) and display an anticarcinogenic property in vivo. References Kashman Y, et al. (1992) J Med Chem 35(15): 2735–2743. Patil AD, et al. (1993) J Med Chem 36(26): 4131–4138. Spino C, et al. (1998) Bioorg Med Chem Lett 8(24): 3475–3478.

Warning: Caution must be taken as the toxic effects of this plant are unknown. Cratoxylum cochinchinense (Lour.) Bl. [From Greek, kratos = strength and xylon = wood and from Latin, cochinchinense = from cochinchina]

Subclass Dilleniidae

153

Synonymy: Cratoxylon polyanthum Korth., Cratoxylon ligustrinum Bl. Common names: Derum seluchor, mampat (Malay).

Physical description: It is a tree which grows to a height of 33 m and a girth of 1.80 m. It is found in the lowland forest from sea level to 500 m in the geographical area covering Malaysia, Burma, Cambodia, Laos, Vietnam, Thailand, the Philippines, South China, and Indonesia.The wood is very hard and durable. The bark is smooth, light buff, and peels off in angular pieces or in long strips. The inner bark is pale cream and the sapwood is yellowish-brown. The stems are greyish, glabrous, and cracked lengthwise. Leaves: simple, decussate and without stipules. The petiole is Fig. 93. Cratoxylum cochinchinense (Lour.) Bl. 2 mm–3 mm long, glabrous, flat above From: KLU Herbarium 34511. Flora of Malaya. and somewhat very thinly edged. The Field collectors: Benjamin C Stone, SC Chin blade is thin, elliptic to spathulate mea- et al., 2 June 1982. Altitude 100 m–500 m. Geosuring 4.7 cm × 1.5 cm–8.4 cm × 3 cm. graphical localization: Kelantan, Bukit Baka The apex of the blade is acute, the Forest Reserve, Malaysia. Botanical identification: Benjamin C Stone, 1983. base is tapered, and the margin is entire and recurved. The blade shows 8–11 pairs of secondary nerves, which are indistinct, and a midrib sunken above and raised below. The flowers are dark red to pink and ephemeral. The fruits are solitary, axillary, green, fusiform, 7 mm × 1.2 cm capsules which beaked at the apex with the rest of the stigmas. The 4 sepals are persistent, fleshy, measuring 7 mm × 4 mm and covering two-thirds of the fruit’s length. The fruits contain 6–8 seeds per locules (Fig. 93). Pharmacological potential:The pharUses: Malays and Indonesians use macological potential of Cratoxylum the leaves and the bark to treat skin cochinchinense (Lour.) Bl is to date diseases. A decoction of the bark is unknown. Note however that this drunk to treat colic, and the resin is plant produces lupeol, (13E,17E)used to control itchiness. ˜ polypoda-7,13,17,21-tetraen-3β-ol, βmangostin, 2-geranyl-1,3,7-trihydroxy-4-(3-methylbut-2-enyl)xanthone and 1,3,7-trihydroxy-2,4-di(3-methylbut-2-enyl)xanthone (Lien HD et al., 1999). It

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will be interesting to learn whether more intensive future research on this family will disclose any molecules of therapeutic interest. O HO

OH R

O

OH

1,3,7-trihydroxy-2,4-di(3-methylbut-2-enyl)xanthone (R = Geranyl)

R

(13E,17E)-Polypoda-7,13,17,21-tetraen-3β-ol (R =β OH)

Reference Lien HD, et al. (1999) Phytochemistry 50(3): 471–476.

Warning: Caution must be taken as the toxic effects of this plant are unknown. Garcinia mangostana L. [After L Garcin (1683–1751), French naturalist and from Malay, mangustan = mangosteen] Physical description: It is a medium-sized Common names: Mangosteen; tropical fruit tree probably native to Southmangostan (French); manggis, east Asia. The bark is yellowish-brown; the mangustan (Malay). inner bark exudates an opaque yellow gum resin. Leaves: simple, without stipules, and decussate. The petiole is 1 cm– 2 cm long, stout, cracked and clasps the stems. The blade is ovate to ovateoblong, leathery, and 6.5 cm–9.5 cm × 3.5 cm–5.5 cm. The apex is acute, and the base is broadly wedge-shaped. The secondary nerves are slender, parallel, 2 mm apart and slightly joining into an intramarginal nerve. The flowers are terminal, the male one in racemes. The perianth consists of

Subclass Dilleniidae

Fig. 94. Garcinia mangostana L. From: KLU Herbarium 18371. Flora of Malaya. Field collector & botanical identification: Lim Ah Lan, June 1973. Geographical localization: Serdang, Malaysia.

4 fleshy sepals and 4 petals. The stamens are numerous and form a slightly 4-lobed mass. The fruits are berries which ripen to magenta, 5 cm in diameter. Its apex is marked by adpressed stigma divided in wedgeshaped lobes. The seeds are embedded in a thick, whitish, edible and juicy pulp (Fig. 94).

155

Uses: By the year 1880, the husk of the fruit of Garcinia mangostana L., exported from the Straits, has become an astringent remedy of great repute which was used to stop diarrhea and dysentery. In Malaysia, a decoction of the roots is drunk to regulate menses. In Indonesia, the leaves and the bark are used to soothe ulcers in the mouth and to treat fever. Very small doses of gum resin are eaten to relieve the bowels of costiveness, but if taken in large doses, it will induce nausea, vomiting, colic, and death.

Pharmaceutical interest: Mangostin: The husk of the mangosteen abounds with prenylated xanthones, which are principally represented by mangostin. Mangostin displays experimentally a remarkable range of pharmacological activities. It inhibits the enzymatic properties of HIV-1 protease (Xing SC et al., 1996), cAMP phosphodiesterase (Chairungsilerd N et al., 1996), calciumdependent ATPases (Furukawa K et al., 1996), cAMP-dependent protein kinase (Jinsart W et al., 1992), and topoisomerase I and II (Tosa H et al., 1997). In addition, mangostin blocks both histaminergic and serotoninergic receptors (Chairungsilerd N et al., 1996a), inhibits the proliferation of methicillinresistant Staphylococcus aureus (Linuma L et al., 1996) and other pathogen microorganisms (Gopalakrishnan G et al., 1997) and is able to scavenge free radicals more efficiently than tocopherol (Yoshikawa M et al., 1994).

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Mangostin also inhibits the conversion of arachidonic acid into PGE2 by cyclooxygenase in microsomal preparations (Nakatani K et al., 2002). A benzenic extract of husk of mangosteen inhibits moderately the tumor-promoting property of teleocidin (Sakai S et al., 1993). Is mangostin involved here? HO

O

OH

OCH3 OH

O

α - Mangostin

References Chairungsilerd N, et al. (1996) Phytochem 43(5): 1099–1102. Chairungsilerd N, et al. (1996a) Planta Med 62(5): 471–472. Gopalakrishnan G, et al. (1997) J Nat Prod 60(5): 519–524. Furukawa K, et al. (1996) Jap J Pharmacol 71(4): 337–340. Jinsart W, et al. (1992) Phytochem 43(50): 1099–1102. Linuma L, et al. (1996) J Pharm Pharmacol 48(8): 861–865. Nakatani K, et al. (2002) Biochem Pharmacol 63(1): 73–79. Sakai S, et al. (1993) Chem Pharm Bull 41(5): 958–960. Tosa H, et al. (1997) Chem Pharm Bull 45(2): 418–420. Xing SC, et al. (1996) Planta Med 62(4): 381–382. Yoshikawa M, et al. (1994) J Pharm Soc Jap 114(2): 129–133.

Warning: Large doses of resin induce nausea, vomiting, colic, and death. Hypericum japonicum Thunb. [From Greek, hyper = above and eikon = picture (the plant was hung above pictures to ward off evil spirit) and from Latin, japonicum = from Japan] Physical description: It is a 30 cm long, Synonymy: Sarothra japonica. erect or procumbent, light green, somewhat succulent herb which grows throughCommon name: Matted St John’s Wort. out Southeast Asia, in China, Japan, Australia, New Zealand, Ceylon, and in the Himalayas. It is found on wet soil, along waterfall paths and by the rivers. The stems are glabrous, smooth, and somewhat 4-winged. Leaves: simple, decussate, amplexicaul, and without stipules. The blade is elliptic, pellucidpunctuates underneath, and 4 mm × 1.5 mm–2 mm × 1 mm. The margin is entire and recurved; the midrib is raised above and below.The flowers are bright yellow, 6 mm–1 cm in diameter and arranged in elongate and dichotomous

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Uses: In China, Hypericum japonicum Thunb. is used to treat skin infection, infectious hepatitis, gastrointestinal disorders, and tumors, to counteract poisoning, soothe inflammation, and to heal abscesses. In Vietnam, the plant is used to heal wounds and leech bites. New Guinea: Hypericum japonicum Thunb. is part of a remedy used to treat malaria.

cymes. The flower pedicels are 6 mm long and the bracts are linearlanceolate. The sepals are lanceolate, Fig. 95. Hypericum japonicum Thunb. From: acute and persistent, and there are 5 KLU Herbarium 24155. Herbarium Jutlandicum petals which are bright yellow and obo- (AAU), Botanisk Institut Aarhus Universitet. Flora of Thailand project, 4th Expedition 1972. vate. The andrecium consists of a few Field collectors: Kai Larsen, Supee S Larsen, stamens, the filaments of which are I Nielsen & T Santisuk. Eastern Thung Kra slightly connate at the base. The ovary Mang. 16◦ 15 North–101◦ 30 East, altitude is single-celled, contains 3 parietal pla- 800 m. Botanical identification: K Larsen. centas and develops 3 styles upward. The fruits are ovoid, 3-valved, dehiscent, and somewhat very thin, 6 mm×3 mm capsules, containing numerous oblong, ribbed seeds that are 0.5 mm long (Fig. 95). Pharmaceutical interest: OH

O

OH

HO

CH3

HO

CH3

Glu-O OH

O

Hypericin

OH

O

OO

OH

HO

H

O

O

OH

OH 1 5 Dihydroxyxanthone glucoside

Isojacareubin-6- O

β D-

Antiviral properties: Like Hypericum perforatum L. (St. John’s Wort), the constituent responsible for the red colour of the juice contained in the dots on the leaves and the flowers of Hypericum japonicum Thunb. is hypericin. This naphthodianthrone has attracted a great deal of interest on account of its antiretroviral properties, and it has even undergone clinical trials as an anti-HIV drug (Lavie G et al., 1989). Hypericin is probably responsible for the anti-HSV-II activity observed by Zheng in 1989.

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Other properties: The antimicrobial activity of Hypericum japonicum Thunb. is attributed to saroaspidin A, B, and C and sarothralin G (Ishiguro K et al, 1987; 1990). Note that the plant produces xanthones, jacarelhyperols A and B, which inhibit Platelets Activation Factor-induced hypotension in vivo (Ishiguro K et al, 2002), as well as 1–5 dihydroxyxanthone-6-O–β–D-glucoside and isojacareubin, which promote and inhibit coagulation in vitro respectively (Wu QL et al., 1998). References Ishiguro K, et al. (1987) Planta Med 53(5): 415–417. Ishiguro K, et al. Planta Med 56(3): 274–276. Ishiguro K, et al. Planta Med 68(3): 258–261. Lavie G, et al. (1989), Proc Natl Acad Sci USA, 86: 5963–5967. Wu QL, et al. (1998) Phytochemistry 49(5): 1395–1402. Zheng MS (1989) J Tradit Chin Med 9(2): 113–116.

Warning: Caution must be taken as the toxic effects of this plant are unknown. Hypericin is a photodynamic sensitizer responsible for cattle poisoning. Mesua ferrea L. [After J. Mesue (777–857), John of Damascus and from Latin, ferrum = iron] Common names: Iron wood tree; mesua naghas (French); penaga (Malay); nagkesara (Indian & Sanskrit). Penaga is a word of Sanskrit origin and the tree has since time immemorial been cultivated in India for its important ceremonial uses.

Physical description: It is a magnificent tree native to India, which grows wild in Burma, Thailand, Indonesia and Malaysia. The wood is very hard, heavy and durable. The bark is dull brown with irregular fissures; the inner bark exudates a clear gum resin. Leaves: green but pinkish-red when young, simple, 6.5 cm–12 cm × 1.5 cm–4 cm, without stipules and decussate. The blade is elliptic, medium sized, tapered at the apex and at the base, bluish below and greenish brown above; and the numerous secondary nerves are hardly visible on both sides. The flowers are showy, ephemeral, fragrant, white, 9 cm in diameter, solitary and axillary. The perianth consists of 4 sepals and petals, and the petals are whitish.The andrecium is showy and consists of several free

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stamens. The gynecium consists of a 1-2-locular ovary, each locule containing 1–2 ovules attached to axillary placentas. The fruits are ellipsoid, shortly beaked, 3 cm in diameter, woody and seated on a persistent calyx, and contain 1–4, woody, glossy seeds with brightly colored partitions (Fig. 96). Uses: In Burma, the flowers of Mesua ferrea L. are used to make an astringent tea and the leaves are used externally to counteract snake-poison. In Malaysia, a bath with these flowers is taken to invigorate health after childbirth. In Indonesia, the pounded seeds or the oil expressed from the seeds are used externally to heal wounds and to treat skin infection.

Fig. 96. Mesua ferrea L.

Pharmaceutical interest: Coumarins: Racemosol and mammea A/AC cyclo F extracted from Mesua racemosa are weakly cytotoxicity towards KB cells (Morel C et al., 1999). It will be interesting to learn whether more intensive future research on Mesua ferrea L. will disclose any coumarins of chemotherapeutic interest.

O

HO

OH

OH

O

O

O

O

O

O

OH OH Racemosol

Mammea A/AC cyclo F

Reference Morel C, et al. (1999) Phytochem 50(7): 1243–1247.

Warning: Caution must be taken as the toxic effects of this plant are unknown.

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C. Order MALVALES Lindley 1833 The order Malvales consists of 5 families and 3500 species of soft-wooded and mucilaginous trees, shrubs, climbers, and herbs thought to have originated side by side with the Lecythidales from the Theales (Appendix I). All the families of this order, i.e. Elaeocarpaceae, Tiliaceae, Sterculiaceae, Bombacaceae and Malvaceae are allied. The Malvaceae, with about 1500 species and the Sterculiaceae with about 1000 species are the largest families.The mucilages of Malva officinalis L., family Malvaceae (marshmallow), Sterculia urens Roxb., family Sterculiaceae (Karaya gum) and Tilia cordata Mill., family Tiliaceae (lime tree) are historically of pharmaceutical usefulness. Note that the seeds often abound with a series of unusual cyclopropenyl fatty acids.

1. Family ELAEOCARPACEAE A. P. de Candolle 1824 nom. conserv., the Elaeocarpus Family Physical description: The family Elaeocarpaceae is the most primitive family of the Malvales. It consists of 10 genera and 400 species of tropical trees, often containing indolizidine alkaO loids derived from ornithine and oxygenated steroids known as N cucurbitacins. In this family, the O leaves are simple, often dark green and glossy on the surIndolizidine alkaloid of Elaeocarpaceae face alternate, simple, occasionO ally siphonostelic, minutely toothed, HO and stipulate. The petiole is long OH O and often bends near the base OH of the blade. The inflorescences HO are racemes, panicles or dichasial cymes. The flowers are regular, R perfect and hypogynous.The calyx comprises of 3–11, free or connate Cucurbitacin D (R = O) sepals connate at the base, and

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valvate.The corolla comprises of 3–5 petals which are valvate and often fringed at the tip. Stamens are numerous and initiated in centrifugal sequence, and often organized into 5 antesepalous groups. The gynecium consists of a single or more carpels united into a compound ovary, each locule containing a pair or several ovules attached to axillary placentas. The fruits are capsules or glossy drupes. Pharmaceutical interest: Elaeocarpaceae are interesting because they elaborate both indolizidine alkaloids and cucurbitacins. Indolizidine alkaloids have attracted a great deal of interest because of their ability to inhibit the enzymatic activity of glucosidases on account of a structural similitude with glucose. Hence, there is some potential in exploring them further in the treatment of HIV, diabetes and cancer. Cucurbitacins are oxygenated steroids with chemotherapeutic potential which have been so far found in the family Cucurbitaceae and Begoniaceae. Aceratium insulare A.C., Elaeocarpus grandiflorus Smith., Elaeocarpus madopetalus Pierre, Elaeocarpus petiolatus Wall., Elaeocarpus floribundus Bl., Elaeocarpus sphaericus (Gaertn.) K. Sch. and Mutingia calaruba are used medicinally in the Asia-Pacific. Elaeocarpus grandiflorus Smith [From Greek, elaion = oil and karpos = fruit, and from Latin, grandis = fullgrown and floris = flower] Physical description: It is a rainforest tree found in Southeast Asia. Leaves: simple, without stipules and alternate. The petiole is 6 mm–3.5 cm long and slightly curved at the base and the apex. The blade is obovate, thinly leathery, and 7 cm–14 cm× 2 cm–5.5 cm. The apex is acute, the base is pointed, and the margin lobed. The blade shows 7–11 pairs of secondary nerves. The inflorescences are axillary 3.5 cm–10 cm long racemes. The flowers are pendulous, showy, 1 cm–1.3 cm long, and develop 5 petals. The fruits are narrowly drupes.

Synonymy: Elaeocarpus hainanensis Oliv. sensu Corner. Common name: Mendong (Malay). Uses: In Indonesia, a decoction of the fruits of Elaeocarpus grandiflorus Smith. is drunk to promote urination, whereas a decoction of the leaves is drunk to reduce urination. A poultice of the bark is applied externally to heal ulcers. The therapeutic potential of Elaeocarpus grandiflorus Smith. is still yet to be discovered.

fusiform, glossy and 1 cm × 3 cm

Warning: Caution must be taken as the toxic effects of this plant are unknown.

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Elaeocarpus sphaericus (Gaertn.) K. Sch. [From Greek, elaion = oil and karpos = fruit, and from Latin, sphaericus = spherical] Common names: Bead tree of India, ustram bead tree; rudraksha (Sanskrit).

Physical description: It is a tree which grows to a height of 15 m in India, Malaysia, Thailand, Indonesia, the Philippines, and the Pacific Islands. The stems are terete, brownish, lenticelled, smooth and glabrous, and the wood is whitish. Leaves: simple, spiral and without stipules. The petiole is 1.2 cm– 1.4 cm long and channeled. The blade is 9 cm × 3 cm–6.7 cm×1.8 cm, rigid and ellipticspathulate. The margin is serrate and Fig. 97. Elaeocarpus sphaericus (Gaertn.) K. Sch. From: KLU Herbarium 005812. Flora of the obscurely recurved. The apex of the Mariana Islands. College of Guam Herbarium. blade is acute and the base is tapered. Field collector: Benjamin C Stone & J Long, 1 The midrib is flat above and raised May 1964. Botanical identification: Benjamin C below, and the blade shows 10–13 Stone 1968. Geographical localization Summit pairs of secondary nerves arching at of Barridaga Hill, approx. 900 feet, limestone forest. the margin. The inflorescences are axillary, 4 cm–6.4 cm long racemes. The flower pedicels are 1.1 cm–1.3 cm long, thin and hairy. The flowers are numerous and fragrant. The calyx comprises of 5 caducous, linear, 1 cm long and hairy sepals. The corolla consists of 5, 1.7 cm × 2 mm, free, white, petals, the apex of which is 5-toothed, each tooth being 5.5 mm long and 3-fid. The ovary is velvety, globose and 2.5 mm in diameter, and develops upwards into a 1 cm long hairy style. The fruits are 2.5 cm in diameter, globose, purple and glossy drupes (Fig. 97). Pharmaceutical interest: Extracts of the fruits (50 mg/Kg–200 mg/Kg i.p, or 200 mg/Kg, per os) show significant antiinflammatory, analgesic, barbiturate-hypnosis potentiation and antiulcerogenic activities in rats and protect guineapigs against the bronchospasm induced by histamine and acetylcholine aerosols (Singh et al., 2000) through stabilization of the release of autacoids from mesenteric mast cells, substantiating

Uses: In India, the dried fruits of Elaeocarpus sphaericus (Gaertn.) K. Sch. are made into buttons and beads by the devotees of Siva, who believe “the beads to be Siva’s tears of rage at the effrontery of mankind”. The fruits are used to treat mental diseases, epilepsy, asthma, hypertension, arthritis, and liver diseases. In the Philippines, the bark is used to treat splenomegaly.

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the efficacy of the plant against bronchial asthma (Singh RK et al., 2000a). An acetone fraction of Elaeocarpus sphaericus displays a marked antimicrobial property (Singh RK et al., 1999). A fraction of mixed fatty acids of Elaeocarpus ganitrus Roxb. inhibits experimentally-induced convulsion (Dasgupta A et al., 1984). It will be interesting to know whether further research on this tree results in the discovery of neuroactive molecules. References Dasgupta A, et al. (1984) Indian J Physiol Pharmacol 28(3): 244–246. Singh RK, et al. (1999) Phytother Res 13(5): 448–450. Singh RK, et al. (2000) Phytotherapy Research 14(1): 36–39. Singh RK, et al. (2000a) Phytomedicine 7(3): 205–207.

Warning: Caution must be taken as the toxic effects of this plant are unknown. Elaeocarpus stipularis Bl. [From Greek, elaion = oil and karpos = fruit, and from Latin, stipula = straw] Common names: Medang tijo, pulai pipit, pinang pergam (Malay).

Physical description: It is a rainforest tree which grows to a height of 18 m in the rainforests of Malaysia, Borneo, Sumatra, the Philippines, and Java. Leaves: simple, alternate, stipulated, leathery, and 15 cm × 3 cm–7 cm. The petiole is 1.5 cm–2 cm long and curved at the base and the apex. The midrib is pubescent. The stipules are 6 mm long. The inflorescences are axillary racemes. The flowers are 7 mm across. The petals and sepals are lanceolate. The andrecium consists of Fig. 98. Elaeocarpus stipularis Bl. 25 stamens which are red and showy. The ovary is hairy, globose and 3–5-locular.The fruits are smooth ovoid, glossy and 1 cm long glossy drupes (Fig. 98). Pharmaceutical interest: It will be interesting to learn whether more intensive future research on Elaeocarpus stipularis Bl. will disclose any antiinflammatory molecules.

Uses: In Malaysia, the leaves of Elaeocarpus stipularis Bl. are pulped and applied externally to soothe inflamed parts.

Warning: Caution must be taken as the toxic effects of this plant are unknown.

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2. Family BOMBACACEAE Kunth 1822 nom. conserv., the Kapok-tree Family Physical description: The family Bombacaceae consists of about 25 genera and 200 species of soft-wooded trees widespread in tropical countries, especially in tropical America. The leaves are simple or palmate, alternate and stipulate; the stipules are deciduous. The flowers are large, hypogynous, and regular. The calyx comprises of 5 sepals which are free or connate at the base and valvate. The corolla consists of 5 petals which are free and convolute. The andrecium comprises of 5 to many stamens initiated in centrifugal sequence. The gynecium consists of 2–8 carpels united to form a compound ovary which encloses as many locules as carpels; with each locule containing 2 ovules or more which are attached to axil placentas. The style is entire or deeply lobed. The fruits are loculicidal capsules often containing arillate seeds. The seeds often contain cyclopropenyl fatty acids. Pharmaceutical interest: Examples of Bombacaceae are Durio zibethinus Murr. (durian tree), Ochroma pyramidale (Cav.) Urban (balsa wood tree), Adansonia digitata L. (baobab) and Ceiba pentandra (L.) Gaertn. (kapok-tree). The resin of Bombax malabaricum DC. is the source of the gum of Malabar which is used in Asia for its tonic, aphrodisiac and haemostatic properties. It will be interesting to learn whether more intensive future research on this family will disclose any molecules of therapeutic interest. Durio zibethinus Murr. [From Malay, duri = thorn and from Latin, zibethum = civet] Physical description: It is a butCommon names: Durian tree; durian tressed tree which grows to a height kampong (Malay). of 40 m. It is native to Sumatra and Borneo, and is cultivated for its valued fruits. The bark is greyish and the wood is yellowish-orange. Leaves: simple, spiral and without stipules. The petiole is 1.5 cm–2 cm long and obscurely winged. The blade is leathery, covered below with silvery or golden stellate scales, elliptic-oblong, and 10 cm–15 cm × 3.5 cm–4 cm. The midrib is sunken above and raised below, the blade shows 12–16 pairs of secondary nerves. The inflorescences consist of cauliflorous and scaly racemes. The flower pedicels are scaly, somewhat

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winged and stout. The flower buds are globose, 1.3 cm × 1.1 cm, and fawn. The flowers are showy, ephemeral, 4 cm long, and comprise a tubular and 5-lobed calyx, and 5 white, spathulate, 2.5 cm × 1.5 cm caducous petals. The stamens are arranged in 5 free bundles and are numerous. The ovary is 5-ribbed and the stigma is protruding. The fruits are large (up to 25 cm × 20 cm), heavy, greenish-yellow, spiny and dehiscent capsules containing a few woody seeds embedded in a yellowish, creamy pulp noted for its fetid smell and agreeable taste (Fig. 99). Uses: In Indonesia, the ash of burned capsules is used to abort a pregnancy and to promote menses, while the juice of the fruit is used to promote venereal desire. In Malaysia, a bath of the leaves is used to treat jaundice, and a decoction of the roots is used to break a fever. It is believed that drinking water from an empty capsule will lower the heat evolved after consumption of its flesh.

Fig. 99. Durio zibethinus Murr.

S

H

H

Hydrogene sulphide H

S

S

H

Hydrodisulphide R

S

S

R’

Pharmaceutical interest: The pecun liar civet smell of durian is partly attributed to a series of polysulphides, Dialkylpolysulphide hydrogen sulphide, 1, 1 diethoxane and ethyl-2-methylbutanoate (Moser R O et al., 1980; Fig. 100). The oil expressed from the seeds is used as a O stabilizer in a patented pesticidal composition (Patent US 4892866). It will be interesting to learn whether more 1,1 - Diethoxyethane intensive future research on this family will disclose any molecules of therFig. 100. Some chemical principles responsiapeutic interest. ble for the peculiar smell of durian.

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D. Order LECYTHIDALES Cronquist 1957 The order Lecythidales consists of the single family Lecythidaceae which is thought to have originated from the Malvales, from the order Theales from where it has inherited the feature of using triterpenoid and tannins as chemical weapons (Appendix I).

1. Family LECYTHIDACEAE Poiteau 1825 nom. conserv., the Brazil-nut Family Physical description: The family Lecythidaceae consists of 20 genera and 400 species of soft-wooded tropical trees known to abound with tannins and saponins. In this family, the leaves are simple, alternate, commonly crowded at the tips of the stems, toothed, glossy, tapered at the base and without stipules. The flowers are ephemeral, epigynous, perfect, showy, and regular. The calyx consists of 2–12 valvate sepals. The corolla consists of 4–6 petals which are free, imbricate and thin. Note that the perianth and the andrecium are often fused and dropped together. The andrecium comprises of numerous stamens either inserted in centrifugal series or gathered in a very characteristic tongue-shaped and succulent body. The gynecium consists of 2–6 carpels united into a 2–6locular, inferior ovary, each locule containing a single or many ovules attached to an axillary or a basal placenta. The fruits are capsular or drupaceous, large and marked at the apex by a conspicuous nectary disc. Pharmaceutical interest: A classical example of Lecythidaceae is Bertholletia excelsia Humboldt & Bompland, the seeds of which are the commercial Brazil-nuts. Another example is Couroupita guianensis Aubl. (canon-ball tree), which is cultivated to decorate parks and other public areas in some tropical countries. In Southeast Asia, Barringtonia acutangula (L.) Gaertn.

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(Barringtonia luzonensis (Presl) Vidal), Barringtonia asiatica (L.) Kurz. (Barringtonia speciosa J.R. & G. Forst., Barringtonia butonica Forst.), Barringtonia racemosa (L.) Spreng., Barringtonia macrostachya (jack) Kurz (Barringtonia cylindrostachya griff.), Careya arborea Roxb., Careya sphaerica Roxb., Chydenanthus excelsus (Bl.) Miers, (Barringtonia vriesii Teijs. & Binn.), and Planchonia papuana R. are used to treat various ailments, including diarrhea, skin problems and rheumatism. Note also that the seeds of several of these plants are used to catch fish on account of their stupefying saponins. It will be interesting to learn whether more intensive future research on this family will disclose any molecules of therapeutic interest such as cucurbitacins. Barringtonia acutangula (L.) Gaertn. [After D. Barrington, an English naturalist of the 19th century, and from Latin, acuere = sharpen and angulus = angle] Physical description: It is a small tree which grows by the river banks and fresh water mangroves, in the geographical zone spanning India to Papua New Guinea. The bark of its stem is greyish and cracked longitudinally. The wood is whitish and soft. Leaves: simple, spiral, without stipules and crowded at the apex of the stems. The petiole is 6 mm–1 cm long and flattened above. The blade is spathulate, 3.2 cm × 1.5 cm–4 cm × 7 cm, glossy, soft, and serrate. The midrib is raised above and below. The blade shows 7– 9 pairs of secondary nerves which are sunke above and raised below. The tertiary nerves are visible and raised above the blade. The inflorescences are terminal and pendulous 20 cm– 30 cm long racemes. The flowers are 6 mm long with a quadrangular receptacle, and have 4 sepals and a conspicuous nectary disk (Fig. 101).

Synonymy: Barringtonia luzonensis (Presl) Vidal.

Fig. 101. Barringtonia acutangula (L.) Gaertn. From: KLU Herbarium 27518. Plants of Ceylon. Geographical localization: Eastern Province, Amparai District, ca. 3 miles Northwest of Maha Oya, altitude 50 m. 3 Dec 1974. Field collectors: Gerrit Davidse & DB Sumithraarachchi.

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Pharmaceutical interest The medicUses: In Burma, Barringtonia acutaninal properties mentioned above are gula (L.) Gaertn. is used to promote yet to be confirmed, but one might appetite, to treat ophthalmia and diarsuppose tannins confer bitterness and rhea. In Laos, Cambodia, and Vietnam, astringency to the plant. The ichthyBarringtonia acutangula (L.) Gaertn. otoxic property of the seeds are conis used to treat gingivitis, diarrhea, firmed experimentally (Chakraborty blenorrhea, menorrhagia and malaria, counteract insect-poisoning, and to DP et al., 1972) and is probably check bleeding. The seeds are also attributed to a series of pentacyclic used there to stupefy fish. In the saponins which include barringtoside Philippines, Barringtonia acutangula A (3-O-β-D-xylopyranosyl(1–>.3)-[β.(L.) Gaertn. is used to heal wounds and .D-galactopyranosyl(1–>2)],-.β D glutreat stomach problems. curonopyranosyl barringtogenol C); barringtoside B, (3.-.O.-β-D.-.xylopyranosyl(1–>3)]β.-.D.-.galactopyranosyl(1–>2)]-β -D-glucuronopyranosyl-21-Otigloyl-28-O-isobutyryl barringtogenol C); and barringtoside C (3-O-α-Larabinopyrano-syl(1–>3)-[β -D-galactopyranosyl(1–>2)]-β D-glucuronopyranosyl barringtogenol C (Pal B.C. et al., 1994). OH OH OH OH HO Barringtogenol C

References Chakraborty DP, et al. (1972) Indian J Exp Biol 1(10): 78–80. Pal BC, et al. (1994) Phytochem 35(5): 1315–1318.

Warning: Caution must be taken as the toxic effects of this plant are unknown. D. Order NEPENTHALES Lindley 1833 The order Nepenthales consists of the Droseraceae (100 species), Nepenthaceae (75 species) and Sarraceniaceae (15 species). Nepenthales are perennial herbs which have evolved with the Malvales from a common ancestry in Theales carnivorous plants forced to adapt habitats deficient in nitrogen (Appendix I). The main chemical weapons used in this order are flavonoids and naphthoquinones.

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1. Family NEPENTHACEAE Dumortier 1829 nom. conserv., the East Indian Pitcher-plant Family. Physical description:The family Nepenthaceae consists of the single genus Nepenthes, with about 75 species of carnivorous, dioecious, tanniferous, erect or prostrate, often epiphytic herbs, which are thought to have originated from the order Theales. Nepenthaceae really stand apart in the Magnolopsida with their leaves which have evolved into pitchers used to trap insects as a source of nitrogen. The inflorescences are racemose or paniculate. The flowers are small, actinomorphic, hypogynous and unisexual. The calyx consists of 3–4 sepals which are imbricate, free, persistent, and glandular within.The andrecium comprises of 4–25 stamens, the filaments of which are united into a column, and the anthers of which are tetrasporangiate, open lengthwise and dithecal. The gynecium consists of 4 carpels facing the sepals which are united into a compound, 4-locular ovary, each locule containing numerous ovules attached to an axile placenta. The fruits are loculicidal capsules containing numerous seeds. Pharmaceutical interest: Nepenthaceae are interO esting because they produce naphthoquinones of CH3 pharmacological interest (these substances justify the regroupment of Nepenthaceae with the Sarraceniaceae and Droseraceae in the order Nepenthales instead of within the order Aristolochiales where they OH O are absent). One such naphthoquinone is plumbagin, which is cytotoxic, irritating and antimicrobial. Plumbagin In the Asia-Pacific, Nepenthes ampullaria Jack and Nepenthes boschiana Korth. are used for medicinal and magic purposes. Little is yet known about the pharmacological potential of the family Nepenthaceae.

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Nepenthes ampullaria Jack ¯ ¯ = griefless and from Latin, ampulla = Roman 2[From Greek, n epenth es handled flask] Physical description: It is a climber found in the rainforests of Malaysia and Indonesia. The stem is terete. Leaves: simple, pitcher-shaped, alternate, sessile and without stipules. The blade is elliptic-spathulate, leathery, 7 cm–20 cm × 2.4 cm–5.2 cm, and rusty tomentose below. The margin is entire and recurved. The midrib sunken above and raised below the blade. The apex of the blade extends into a 2 cm–7 cm long velvety tendril of terminated with or without a light green, broad, 7 cm × 5.8 cm–5.3 cm × 4 cm pitcher (Fig. 102). Uses: In Malaysia, a decoction of the roots of Nepenthes ampullaria Jack is drunk to treat dysentery and to assuage stomachache.

Common names: Akar tekuyot (Malay).

Fig. 102. Nepenthes ampullaria Jack. From: KLU Herbarium 32151. Flora of Malaya. University of Malaya Herbarium. Field collector & botanical identification: Benjamin C Stone, 23 Nov 1980. Geographical localization: Johor, Kota Tinggi, ridge forest, dipterocarps, altitude: 1000 ft Malaysia.

Pharmaceutical interest: The pharmacological potential of Nepenthes ampullaria Jack is still waiting to be discovered. The use of this plant may be on account of its astringency. Note that a series of antimalarial naphthoquinones, including plumbagin, 2-methylnaphthazarin and droserone, have been characterized from the roots of Nepenthes thorellii (Likhitwitayamuid K et al., 1998). Such naphthoquinones are probably present in Nepenthes ampullaria Jack. Reference Likhitwitayamuid K, et al. (1998) Planta Med 64(3): 237–241.

Warning: Caution must be taken as the toxic effects of this plant are unknown.

2. Family DROSERACEAE Salisbury 1808 nom. conserv., the Sundew Family. Physical description: The family Droseraceae consists of 4 genera and about 100 species of discrete perennial herbs forming rosettes of leaves, which

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are often circinate in buds and usually covered with sticky stipitate glands or marginal bristles which entrap insects. Naphthoquinones and flavonoids are known to occur in this family. The inflorescences are simple and circinate cymes of bisexual flowers. The calyx comprises of 4–5 sepals which are imbricate and persistent. The corolla consists of 5 petals which are hypogynous and free. The anthers are 2-locular, extrorse, and open by longitudinal slits. The gynecium consists of 3–5 carpels united to form a compound and unilocular ovary containing 3 to numerous anatropous ovules attached to central or parietal placentas. The fruits are loculicidal capsules containing several spindle-shaped seeds. Pharmaceutical interest: A classical example of DroserO aceae is Dionaea muscipula (Venus’s flytrap), which has CH3 attracted a great deal of interest on account of its leaves which entrap insects. Traditionally used in Europe to treat OH spasms, soothe and calm cough were Drosera rotundifoOH O lia L., Drosera anglica Huds. (Drosera longifolia L.) and Drosera intermedia Hayne (sundews, red roots). The airDroserone dried entire Drosera rotundifolia (Drosera, French Pharmacopoeia, 1965) has been used to treat chronic bronchitis, asthma, and whooping cough, usually as tincture (1 in 5; dose 0.5 mL– 2 mL). D naphthoquinones including plumbagin and droserone, which are irritating and antibacterial against a broad spectrum of Gram-positive and Gramnegative organisms, fungi and protozoa (Leishmania, Plasmodium). Drosera burmannii Vahl, Drosera rotundifolia L., Drosera indica L., and Drosera peltata Sm. are of medicinal value in Southeast Asia. Not much is yet known about the pharmacological potential of the family Droseraceae. Drosera burmannii Vahl [From Greek, droseros = dewy and after N.L. Burmann, 18th century Dutch botanist] Physical description: It is a little herb found Common names: chin ti lo in the wet grassland and sandy heaths (Chinese); co troi ga (Vietnam). of India, Japan, Malaysia, Australia, China, Cambodia, Ceylon, Thailand, Laos and Vietnam. The plant grows from a tiny reddish rosette of leaves. Leaves: small, 4 mm × 3 mm–6 mm × 16 mm, orbicular and covered with sticky, stipitate, moving, glittering and reddish glands. The inflorescences are cymes on top of 8 cm–13 cm tall erect stems. The flower pedicels are 2.5 mm long. The calyx is red and comprises of a few lanceolate and 2.5 mm × 1.5 mm sepals. The corolla is white and very thin. The anthers are yellow (Fig. 103).

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Uses: In China, Drosera burmannii Vahl is used to treat dysentery, scrofula and malaria. In Laos, Cambodia and Vietnam, Drosera burmannii Vahl is used to treat whooping cough and spasms.

Pharmaceutical interest: The medicinal properties of Drosera burmannii Vahl await experimentation. Note however that the antidysenteric property mentioned above could involve the astringency of tannins as well as antibacterial/antiplasmodial naphthoquinones, such as plumbagin from Drosera peltata which inhibits the Fig. 103. Drosera burmannii Vahl. From: KLU growth of oral bacteria cultured in vitro Herbarium 12440. Plants of Cambodia. University of Malaya Herbarium. Field collector: Ben(Didry N et al., 1998). jamin C Stone, 7 Mar 1970. Geographical local-

Flavonoids: In regard to the antispas- ization: Mt. Kam Chai, Poporkville. Botanical modic properties of Drosera species, identification: JE Vidal 2/1973. a number of experiments conducted in vitro tend to demonstrate that the binding of flavonoids to cholinergic and histaminic decreases the contraction of smooth muscles. As an example, ethanolic extract of Drosera madagascariensis (0.5 mg/mL–1 mg/mL) containing quercetin, isoquercitrin and hyperOH oside, relaxes isolated portions of guineaOH pig ileum through cholinergic receptors and histamine H1 receptors, respectively. Note HO O that quercetin (IC50 0.8 µg/mL), hyperoside (IC50 0.15 µg/mL) and isoquercitrin (IC50 0.7 OH µg/mL) inhibit human neutrophil elastase OH O with an IC50 of 9.4 µg/mL (Melziq MF et al., Quercetin 2001). References Didry N, et al. (1998) J Ethnopharmacol 60(1): 91–96. Melziq MF, et al. (2001) Phytomed 8(3): 225–229.

Warning: Caution must be taken as the toxic effects of this plant are unknown.

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Drosera indica L. [From Greek, droseros = dewy and from Latin, indica = from India] Common name: Uses: In Laos, Cambodia and Vietnam, Drosera indica L. is used to soothe callosities and corns. The pharmacological potential of Drosera indica L. is still waiting to be discovered.

Physical description: It is a tiny herb which grows to a length of 30 cm. It is found in India, Burma, China, Australia, Vietnam, Laos, and Cambodia. Leaves: alternate, simple, tentacleshaped, 5 cm long, channeled, and covered with microscopic infundibuliform sticky and moving hairs. The Fig. 104. Drosera indica L. From: KLU Herbarinflorescences are axillary cymes of ium 30687.The Forest Herbarium (BKF), Royal 5.5 cm–20 cm in length. The pedicels Forest Department. Flora of Thailand. Geographical localization: Burirum, altitude: 130 m, are 6 mm–13 mm long. The calyx con- 27 Nov 1978. Field collectors: C Phengklai et al. sists of 5 oblong sepals united at Botanical identification: Shamlong. the base, 1.5 mm long and hairy. The corolla consists of 3-lobed, white, 3.5 mm × 4 mm, and spathulate petals. The fruits are dehiscent 3-lobed capsules, which are smooth, glossy, and crowned with a few membranous fragments of corolla. The seeds are very small, black, and longitudinally ribbed (Fig. 104). Warning: Caution must be taken as the toxic effects of this plant are unknown. D. Order VIOLALES Lindley 1833 The order Violales consists of 24 families and about 5000 species of plants which are thought to have originated, alongside with the Capparales, from the order Theales, somewhere near to the Malvales (Appendix I). In regard to the chemical repellents used in this order Datiscaceae, Cucurbitaceae and Begoniaceae use steroidal saponins, Ancistrocladaceae and Dioncophyllaceae use of isoquinoline alkaloids and cyanogen glycosides and cyclopentenic fatty acids are common in Passifloraceae and Flacourtiaceae. The family Flacourtiaceae is the most archaic family of the order Violales and is thought to connect the Theales to the Violales.

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1. Family FLACOURTIACEAE A. P. de Candolle 1824 nom. conserv., the Flacourtia Family Physical description: The family Flacourtiaceae consists of 85 genera and more than 800 species of tropical trees or shrubs. The leaves are simple, alternate, and pellucid-dotted or lined, and the stipules are often deciduous. The flowers are dioecious or polygamous, and often hypogynous. The calyx comprises of 3–15 sepals which are free, imbricate and alternate with the petals. The corolla comprises of 3–15 petals which are free, imbricate, and occasionally not distinguishable from the sepals. The andrecium consists of several stamens arranged in bundles opposite to the petals. The anthers are 2-celled and open by longitudinal slits. The gynecium consists of 2–10 carpels forming a compound, superior, and single-celled ovary containing 2 to several ovules. The ovules are anatropous to amphitropous or orthotropous, and are attached to parietal placentas. The styles are free or united to varying degrees, and the stigmas are distinct. The fruits are berries, or capsules or drupes. The seeds are often embedded in an aril. COOH COOH

Hydnocarpic acid

Chaulmoogric acid

Pharmaceutical interest: The freshly expressed oil of the seeds of Casearia sylvestris (Brazil), Hydnocarpus alcalae C. DC. (Filipino), Hydnocarpus anthelminticus Pierre (lukrabo or ta fung tsze seeds, Cambodia, Laos, Vietnam), Hydnocarpus wightiana (India), Oncoba echinata (gorli oil) and Hydnocarpus kurzii (King) Warb. (Chaulmoogra oil), has been used externally since a very remote period in time to treat leprosy. This oil contains a unique class of cyclopentenic fatty acids, such as chaulmoogric acid (13-cyclo-pent-2-enyl-n-tridecanoicacid), hydnocarpic acid and gorlic acid, which destroy Mycobacterium leprae. Another example of medicinal Flacourtiaceae is Aphloia madagascariensis Clos., which appears in a few proprietary drugs used to promote urination. About 20 species of plants classified within the family Flacourtiaceae are used for medicinal purposes in Southeast Asia. Note that the oil expressed from the seeds is often used to treat skin diseases. Casearia grewiaefolia Vent. [After J Caesarius (1642–1678), preacher in Dutch East India Company and from Latin, grewiaefolia = leaves like Grewia] Physical description: It is a rainforest tree which grows to a height of 24 m and a girth of 180 cm. The stems are softly hairy and slightly zigzag-shaped.

Subclass Dilleniidae

Leaves: simple, stipulate, 10 cm × 3.5 cm and spiral. The stipules are deciduous. The blade is tomentose below, oblong, tapered at the apex and squarish at the base, and shows about 20 pairs secondary nerves. The inflorescences are clusters on stems behind leaves. The fruits are globose, ribbed, with persistent calyces, and contain a few seeds embedded in a juicy aril. Warning: Caution must be taken as the toxic effects of this plant are unknown.

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Synonymy: Casearia hexagona Decne, Casearia laurina Blume, Casearia leucolepis Turcz. Common name: Big-leaved caesaria; utong manok (Indonesian). Uses: In Cambodia, a decoction of the bark is drunk to invigorate health after childbirth. It will be interesting to learn whether a more intensive study on this plant will disclose any cytotoxic clerodane diterpenes such as casearvestrins reported Casearia sylvestris (Oberties NH et al., 2002).

Reference Oberties NH, et al. (2002) J Nat Prod 65(2): 95–99.

Flacourtia rukam Zoll. & Mor. [After E de Flacourt (1607–1660), a French Governor of Madagascar, and from Malay, rukam = Flacourtia rukam Zoll. & Mor.] Uses: The ripe berries of Flacourtia rukam Zoll. & Mor. are acid and astringent, but rubbing them between the hands bruises the flesh and renders it sweet and palatable. In Indonesia, the sap expressed from young shoots is used to wash the eyes. In Malaysia, the juice expressed from the berries is ingested to stop diarrhea and dysentery. The sap expressed from the leaves is applied to inflamed eyelids. The powdered dried leaves are used to heal wounds. In the Philippines, a decoction of the roots is drunk to invigorate health after childbirth. The pharmacological properties of Flacourtia rukam Zoll. & Mor. are unknown til to date.

Synonymy: Hiaingera grandiflora Turez, Flacourtia inermis Merr. Common name: Indian prune.

Fig. 105. Flacourtia rukam Zoll. & Mor.

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Physical description: Flacourtia rukam Zoll. & Mor. or Indian prune is a small rainforest tree of Southeast Asia. The trunk and the stems are covered with strong and up to 4 cm long woody thorns. The bark is soft and yellowish, and the wood is hard, sappy and heavy. Leaves: simple, spiral, without stipules, and 11 cm–17cm × 4 cm–10 cm. The blade is tapered at the apex into a 1 cm– 2 cm long tail. The base of the blade is broadly wedge-shaped. The margin is lobed.The inflorescences are very small axillary clusters of whitish flowers.The fruits are glossy, red and 2.5 cm long, crowned with a ring of peg-like persistent styles (Fig. 105). Warning: Caution must be taken as the toxic effects of this plant are unknown. Hydnocarpus species [From Greek, hudron = truffle and karpos = fruit] Physical description: Forty species of Common name: Setumpol (Malay). Southeast Asian trees make up the genus Hydnocarpus Gaertn. The bark of Hydnocarpus species is smooth. Leaves: simple, spiral and stipulate. The stipules are deciduous. The petiole is woody, transversally cracked, and bends at the base.The blade is leathery, asymmetric at the base, and the margin is entire. The inflorescences are small and cymose clusters of unisexual flowers. The calyx consists of 4–5 deciduous sepals. The corolla comprises of 4–5 petals which are papery and scaly inside at the base. The andrecium consists of 5 to several stamens. The ovary is sessile and encloses 3 placentas. The stigmas consist of 3–5 long branches. The fruits are large, rugose, and woody capsules containing several seeds packed in a pulp. Pharmaceutical potentials: Anti-mycobacterial properties: Uses: In the Asia-Pacific, the oil expressed The fixed oil expressed from from the seeds of Hydnocarpus anthelmintithe fresh ripe seeds of Hydnocus Pierre, Hydnocarpus kurzii (King) Warb., carpus wightiana, Hydnocarpus Hydnocarpus hainanensis Merr., and Hydnoanthelminticus Pierre, Hydnocarcarpus alcalae C. DC.) is applied externally pus kurzii (King) Warb. (Tarakto treat leprosy and other skin infections. togenos kurzii ) and Hydnocarpus heterophylla is Hydnocarpus oil or chaulmoogra oil (International Pharmacopoeia, 1967). Chaulmoogra oil was the only effective treatment for leprosy for centuries until the recent arrival of chemotherapeutic agents. The active principles involved here are a series of unusual cyclopentenic unsaturated fatty acids such as chaulmoogric acid, the mode of action of which is still unknown. Both Wistar rats experimentally-wounded (Oommen ST et al., 1999) and mice infected with resistant Mycobacterium leprae, recovered when fed with a mixture consisting of Hydnocarpus oil and dapsone (Desai AC et al., 1977). Healing properties: In regard to the dermatological property of Hydnocarpus oil, a number of experiments conducted both in vitro and in vivo tend to

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demonstrate that the oil of Hydnocarpus heals wounds and could be of value for making cosmetics. Hydnocarpus oil increases body weight, strengthens collagen tissue and increases the production of hydroxyproline in male. Other properties: Hydnowightin, hydnocarpin and neohydnocarpin, 3 flavolignans characterized from Hydnocarpus wightiana, lower both serum cholesterol and triglyceride levels in rodents. Hydnocarpin is also anti-inflammatory in vivo, and all the compounds annihilate the survival of a number of cancer cell-lines cultured in vitro (Sharma DK et al., 1991). An alcoholic extract of the seeds of Hydnocarpus wightiana inhibits the proliferation of Human Ascaris lumbricoides cultured in vitro (Raj RK, 1975). References Desai AC, et al. (1977) Lepr India 49(3): 360–363. Oommen ST, et al. (1999) Int J Lepr Other Mycobact Dis 67(2): 244–246. Raj RK, (1975) Indian J Physiol Pharmacol 19(1). Sharma DK, et al. (1991) J Nat Prod 54(5): 1298–1302.

Warning: Caution must be taken as the toxic effects of this plant are unknown. Pangium edule Reinw. [From Indonesian, pangi = a name and from Latin, edule = edible] Physical description: It is a tree which grows to a height of 25 m and a girth of 45 cm. It is found wild or Common name: Kepayang (Malay); penace (Indonesian). Uses: In Indonesia, a cold water infusion of fresh leaves or seeds is applied externally to counteract putrefaction and expel parasites. In Indonesia, Malaysia, and Papua New Guinea, the seeds are eaten after careful preparation to remove cyanides. The plant is also used in Malaysia to preserve meat and the oil expressed from the seeds is used for food. It will be interesting to learn whether more intensive future research on this family will disclose any molecules of therapeutic interest.

Fig. 106. Pangium edule Reinw. From: KLU Herbarium 043112. Herb. Lugd. Batav. Field collector & botanical identification: Ave´ 23.1.83. Geographical localization: Kampung Sekam, Northeast of Tapah, Perak, West Malaysia, 4◦ 20 North–101◦ 20 East, altitude 600 m. From: KLU Herbarium 039560. Flora of Sulawesi Selatan. Field collector & botanical identification: SC Chin, 13 June 1986. Geographical localization: Karaenta Park, near the 56 km milestone from Ujung Pandang.

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cultivated throughout the Asia-Pacific where it has manifold uses. The bark is brown and smooth; the inner bark is orange-yellow. The stems are velvety when young. Leaves: simple, spiral, without stipules, crowded at the apex of the stems.The petiole is 9 cm–16 cm long and thin.The blade is 15.7 cm×16.3 cm– 24.1 cm×26.3 cm, papery, glabrous, and cordate or somewhat 3-lobed, and the margin is recurved.The blade shows 6–9 pairs of secondary nerves and tertiary nerves which are scalariform. The flowers are 1.5 cm–2.5 cm long and green. The fruits are 9 cm–14 cm in diameter, scurfy, brownish, bluntly tipped at both ends, hanging from long pedicels of 8 cm–15 cm long, in groups and contain several 5.8 cm × 4.4 cm × 2 cm warty seeds (Fig. 106). Warning: All parts of this plant and especially the seeds are poisonous because of hydrocyanic acid which is released from gynocardin. The bark and the leaves are used to poison fish, so that they rise to the surface to be harvested. Xylosma congesta (Lour.) Merr. [From Greek, xylos = wood and osma congestionem = congested] Physical description: It is a small tree found in Southeast Asia and China. The stems are glabrous. Leaves: simple, rhomboid, 2.5 cm–3.5 cm, and obscurely serrate. The flowers are dioecious and arranged in axillary short cymes. The male flowers are 3 mm long, comprise of 5 imbricate sepals and several stamens. The fruits are globose berries containing several seeds. Pharmaceutical interest: The therapeutic potential of this plant is unexplored yet. Xylosmacin, a phenyl glucoside, was characterized from Xylosma velutina by Cordell et al. (1977).

=

smells and from Latin,

Synonymy: Croton congestum Lour., Xylosma racemosum Miq., Xylosma japonicum A. Grey, Xylosma apactis Koidz., Xylosma congestum (Lour.) Merr. Xylosma senticosum, Myroxylum senticosum. Common names: Tung ch’ing (Chinese).

Uses: In China, the ash of the bark is mixed with water and the mixture is drunk to treat jaundice and tumors, heal scrofulous sores and to induce delivery in labor. The roots are used to facilitate parturition.

Reference Cordell GA, et al. (1977) Lloydia 40(4): 340–343.

Warning: Caution must be taken as the toxic effects of this plant are unknown.

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2. Family BIXACEAE Link. 1831 nom. conserv., the Lipstick-tree Family Physical description: The family Bixaceae consists of 3 genera and about 20 species of tropical shrubs. In this family, the leaves are simple, alternate, stipulate, palmately nerved, lobed or compound. The flowers are hermaphrodite, showy, hypogynous and arranged in panicles or racemes. The calyx consists of 5 distinct, imbricate, deciduous sepals, and the corolla consists of 5 large, imbricate, and convolute petals. The andrecium consists of several stamens initiated in a centrifugal sequence, the anthers of which are horseshoe-shaped. The gynecium consists of 2–5 carpels forming a singlelocular ovary containing several ovules attached to parietal placentas. The style is long and thin, and the stigma forked. A nectary disc is present. The fruits are densely echinate-setose or smooth, bi-valved capsules, containing several seeds the testa of which is succulent and red. Pharmaceutical interest: The seeds of Bixa orellana L. (lipstick tree) contain annatto, which is a permitted dye for food, drugs and cosmetics. The estimated world production of annatto seeds is 4000 tons from Ecuador, India, Kenya and Peru. Although interest in annatto has dramatically declined with the advent of synthetic dyes, its use is steadily increasing since it is a non toxic food additive. Thus far, no molecule of pharmacological interest is known to exist in this family. Bixa orellana L. [From South American, bixa = Bixa orellana L.] Physical description: It is a shrub or Common names: Annatto, lipstick small evergreen tree native to northern tree; thideng, thidin (Burmese); South America. It is widely cultivated chompuh chralok (Cambodian), cham for its seeds or as an ornamental plant pu, xiem phung (Chinese); arnatto, in the West Indies, tropical Asia and roucou, roucouyer, anate (French); Africa. Leaves: simple and spiral. The achiote, anate (Filipino); arnotto petiole is 5 cm–7.5 cm long. The blade (Portuguese); sinduri, virpushpa (Sanskrit); avam (Tamil). is 10 cm–20 cm×6.3 cm–12.5 cm, dark green, ovate, acute or acuminate, truncate or subcordate at the base and glabrous. The flowers are 5 cm in diameter, showy, and arranged in terminal panicles. The pedicels are pubescent. The calyx consists of 2 small concave sepals and 3 large oblong sepals. The corolla comprises of 5 pinkish or white obovate petals which are very thin. The andrecium comprises of numerous stamens. The fruits are dehiscent, ovoid or subglobose capsules clothed in slender prickles and containing 15–20 trigonous seeds embedded in a bright red pulp (Fig. 107).

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Division MAGNOLIOPHYTA Uses: In Cambodia, the leaves of Bixa orellana L. are used to treat fever. In Indonesia, the water in which the leaves of Bixa orellana L. were rubbed is poured over the head of children to treat fever. In Malaysia, the leaves are used in a postpartum medicine. In the Philippines, the leaves are pounded in coconut oil and heated, then applied to the abdomen to relieve tympanites. A paste made from the fresh leaves is used to make a rubefacient remedy, and a decoction of the leaves is used to stop dysentery. The unripe fruits are used as an emollient to treat leprosy. A decoction of the bark is drunk to treat febrile catarrh. In Cambodia, Laos, and Vietnam, a lotion or a bath of the leaves is used to treat fever, and an infusion of the seeds is drunk to treat asthma and excessive secretion of mucus from the nasopharynx. An alcoholic extract of the seed coat is eaten to expel intestinal worms and relieve the bowels of costiveness. In Taiwan, the seeds are astringent and used to treat fever.

Fig. 107. Bixa orellana L.

Pharmaceutical interest: The coloring principle of annatto is bixin, a C24 apocarotenoid first isolated in 1875, which represents 2.5% (dry weight) of the seeds. Annatto is extracted with water and used to dye food (European identification code E160b, maximum daily allowance: 2 mg/Kg). Like many other carotenoids, bixin is antioxidant and is able to scavenge free radicals. In vitro bixin scavenges superoxide anions generated by the xanthine/xanthine oxidase more efficiently than lutein and β-carotene (Zhao W et al., 1998). Irradiated rats (10Gy.) fed with bixin at 200 µM/Kg have less lung collagen hydroxyproline and less serum and liver lipid peroxydation (Thremsiamma KC et al., 1996). Trans-bixin characterized from annatto decreases the glycaemia in anaesthetized dogs. The electron microscopy of portions of pancreas and liver revealed damaged mitochondria and endoplasmic reticulum suggesting a possible risk of diabetes (Morrison EY et al., 1991). Annatto intake results in a decrease of IgE production by rat spleen lymphocytes at 10 µM (Kuramoto Y et al., 1996). However, the absence of carcinogenic and anticarcinogenic effects of annatto in the rat liver medium-term assay has been observed (Agner AR et al., 2004). COOCH3

HOOC Bixin

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References Agner AR, et al. (2004) Food and Chemical Toxicology, 42(10): 1687–1693. Kuramoto Y, et al. (1996) Biosci Biotechnol Biochem 60(10): 1712–1713. Morrison EY, et al. (1991) Trop Geogr Med 43(1–2): 184–188. Thremsiamma KC, et al. (1996) Ind J Exp Biol 34(9): 845–847. Zhao W, et al. (1998) Biochim Biophys Acta 138(1): 77–88.

Warning: The leaves and unripe fruits are said to irritate the skin and mucosa. Adverse reactions associated with annatto dye are possible and include urticaria and angiooedema. A patient developed urticaria, angiooedema and hypotension within 20 days following the ingestion of fibers containing annatto. The non-dialyzable fraction of annatto dye on SDS-PAGE demonstrated 2 proteins staining bands in the 50 KDa range.

3. Family ANCISTROCLADACEAE Walpers 1851 nom. conserv., the Ancistrocladus Family Physical description:The family Ancistrocladaceae is a little group of obscure woody climbers confined to the tropical rainforests of Southeast Asia, India and Africa. The leaves are simple, lanceolate, leathery and stipulate. The flowers are small, bisexual, and paniculate with recurved branches. The calyx is tubular, 5-lobed and accrescent in fruits. The corolla comprises of 5 contorted petals. The andrecium comprises of 5–10 stamens. The gynecium comprises of 3 carpels forming an inferior and single-celled ovary which encloses a subbasal ovule. The ovary shows 3 styles at the apex. The stigma is enlarged and lobed. The fruits are winged nuts containing a few seeds. Pharmaceutical interest: Ancistrocladaceae are interesting because they produce naphthylisoquinoline alkaloids. These very unusual alkaloids have attracted a great deal of interest on account of their activity against Plasmodium falciparum, the Human Immunodeficiency Virus and several sorts of cancer cell-lines. Ancistrocladus heyneanus, Ancistrocladus barteri and Ancistrocladus tectorius (Lour.) Merr., are used to treat malaria in several tropical countries. Ancistrocladus tectorius (Lour.) Merr. [From Greek, ancistr = fish hook, klados = branch; and from Latin, tectorius = forming a covering] Physical description: It is a climber found on the seashores of Thailand, Cambodia, Laos, Vietnam, Malaysia and Indonesia. The stems develop from the axil of hooks. Leaves: simple,

Synonymy: Ancistrocladus pinangianus. Common names: Akar julong hitam; lindah sapi (Malay).

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hard, lanceolate and 5 cm–10 cm × 15 cm–30 cm. The blade shows 7–10 pairs of secondary nerves. The inflorescences are axillary, long and thin panicles of small dark red flowers. The flowers consist of 5 sepals, 5 petals, 10 stamens, and a half inferior ovary. The fruits are nuts with persistent, asymmetrical, oblong, 5 cm × 1.5 cm, subspathulate, obtuse, and brown sepals (Fig. 108). Uses: In Malaysia, a decoction of the roots of Ancistrocladus tectorius (Lour.) Merr. is drunk to stop dysentery and to treat malaria. Fig. 108. Ancistrocladus tectorius (Lour.) Merr.

Pharmaceutical interest: Antiplasmodial properties: In regard to the antiplasmodial properties of the Ancistrocladus species, a number of experiments conducted in vitro clearly demonstrate that naphthylisoquinoline alkaloids are the active principles. 10 µg/mL of a crude alkaloid fraction from Ancistrocladus sp. annihilates efficiently Plasmodium berghei cultured in vitro in human hepatoma cells (HepG2). Dichloromethane extracts of Ancistrocladus abbreviatus and Ancistrocladus tectorius (Lour.) Merr. exhibit levels of anti-plasmodial activities comparable to primaquine (25 µg/mL; 62.1% against 27.7%–70%; Francois G et al., 1997). Small concentrations (about 2 µg/mL) of korupensamines A, B, C or D from the leaves of Ancistrocladus korupensis destroy in vitro half of the asexual erythrocyte stage of Plasmodium falciparum and Plasmodium berghei (Hallock YF et al., 1997). Extracts of Ancistrocladus abbreviatus, Ancistrocladus barteri and purified naphthylisoquinoline alkaloids inhibit the asexual erythrocyte stage of Plasmodium falciparum (K1/chloroquine-resistant and NF 54/64, clone A1A9/chloroquine-sensitive; Francois G et al., 1994). Note that betulinic acid, from Ancistrocladus heyneanus annihilates the asexual erythrocyte stage of Plasmodium falciparum cultured in vitro (Bringmann G et al., 1997). Antiviral properties: Michellamine B, D, E and F characterized from Ancistrocladus korupensis inhibit in vitro the replication of the Human Immunodeficiency Virus (Hallock YF et al., 1997). Michellamine B acts at both stages of the Human Immunodeficiency Virus life cycle by inhibiting both reversetranscriptase and the cells fusion in syncytium (Mac Mahon JB et al., 1995). Michellamine B inhibits the killing of cells and viral replication in a variety of

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human cell-lines and human peripheral blood leukocytes and monocytes. It acts against a panel of pharmacologically diverse laboratory and clinical strains of Human Immunodeficiency Virus type-1 including the AZT-resistant strain G-910-6, the pyridinone-resistant strain A-17 and a number of Human Immunodeficiency Virus type-2 strains (Boyd MR et al., 1994). Cytotoxic properties: Dioncophylline A, characterized from Ancistrocladus abbreviatus and from the closely related family Dioncophyllaceae, inhibit the proliferation of the National Cancer Institute panel of human tumor cell-lines (Hallock YF et al., 1995) and annihilate Biomphalaria glabra (LD50 : 20 ppm).

OH HN

References Boyd MR, et al. (1994) J Med Chem 37(12): 1740–1745. Bringmann G, et al. (1997) Planta Med 63(3): 255–257. Francois G, et al. (1994) Phytochem 35(6): 1461–1464. Francois G, et al. (1997) Int J Parasitol 27(1): 29–32. Hallock Y, et al. (1997) J Nat Prod 60(7): 677–683. Mac Mahon JB, et al. (1995) Antimicrob Agents Chemother 39(2): 484–488. Manfredi KP, et al. (1991) J Med Chem 34(12): 3402–3405.

OH OH

OCH3

OCH3 OH HO HH OH Michellamine

Warning: Caution must be taken as the toxic effects of this plant are unknown.

4. Family CARICACEAE Dumortier 1829, nom. conserv., the Papaya Family Physical description: The family Caricaceae consists of 4 genera and about 30 species of tropical and subtropical laticiferous soft-stemmed small trees and shrubs. The leaves of Caricaceae are alternate, large, long-petioled, digitately lobed or foliolate and without stipules. The inflorescences are cymose and axillary. The flowers are hermaphrodite or unisexual, regular and hypogynous. The calyx comprises of 5 very small sepals united into a lobed calyx.The corolla comprises of 5 petals united into a long and thin tube, the lobes of which are convolute or valvate. The andrecium consists of 2 whorls of 10 stamens, the filaments of which are attached to the corolla tube, free or connate at the base; and the anthers of which are tetrasporangiate and dithecal, and endowed with a shortly prolonged connective, and with pollen sacs opening by longitudinal slits. The gynecium consists of 5 carpels united into a compound 1-locular or spuriously 5-locular superior and sessile ovary, each locule containing several

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ovules attached to parietal placentas. The fruits are large, smooth, green, and ovoid berries, containing several seeds with a succulent endosperm and a straight embryo. An example of Caricaceae is Carica papaya L., the fruits of which are palatable.

Common names: Papaya, melon tree; figuier des iles, figuier des negres, ˆ melon des tropiques, papayer (French); pimbosi, simbosi, thimbaw, timbosi (Burmese); lohong si phle (Cambodian); pohunbetek (Malay); chirbhita (Sanskrit); pappali (Tamil).

Carica papaya L. [From Greek, karike, a kind of fig and from papaya = the Caribbean word for Carica papaya L.] Physical description: It is a small fruit tree native to Central America. The bole is soft-wooded, marked with conspicuous leaf-scars and laticiferous. Leaves: 30 cm–60 cm, glabrous, palmatifid and palmatinerved. The petiole is about 30 cm long, fleshy and thin. The flowers are light yellow, slightly fragrant, and generally dioecious. The male flowers are arranged in long dropping panicles. The female flowers are arranged in short clusters. In the female flowers, the ovary is single-locular and the stigma is sessile, 5-lobed and lacerated. The fruits are succulent, indehiscent, single-celled, ovoid to oblong, greenish-yellow, smooth and 15 cm × 30 cm berries.The flesh is red, juicy and palatable.The seeds are numerous and black, and taste like capper (Figs. 109 & 110). Pharmaceutical interest: Papain: The latex of Carica papaya L. contains a mixture of cysteine proteinases, chiefly represented by papain, chymopapain and papayoproteinase . Cysteine proteinases, which are responsible for a variety of cellular processes including the cartilage degradation in arthritis, the progression of Alzheimer’s disease and cancer invasion, are of immense pharmacological

Fig. 109. Carica papaya L.

Subclass Dilleniidae

Fig. 110. Carica papaya L.

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Uses: In Burma, the latex of Carica papaya L. is used to expel intestinal worms and to remove the false membrane of diphtheria. In Cambodia, the seeds are used to counteract insect poison, and a poultice of the roots is used to treat uterine tumors. The roots are used to control excessive menses and to expel urinary stones. In Indonesia, the latex is used to expel intestinal worms and to counteract snake-poison. The roots and the seeds are used to expel intestinal worms. In China, the pulp of the fruit is applied to swollen and inflamed feet. In Malaysia, a paste made from the roots is rubbed all over the body after childbirth, and the seeds are ingested in the early months of pregnancy to abort it. The latex is used to remove skin patches. In the state of Kelantan, the latex of the unripe fruit was used as a poison for criminal purposes. In Cambodia, Laos, and Vietnam, the latex is used to expel intestinal worms, remove warts and corns, and to treat eczema and psoriasis. The tree was spread all over the tropics by early Portuguese and Spaniards who discovered it in South America.

importance. Papain is a protein consisting of 212 amino acids with a molecular weight of about 23 000 Daltons. Pure chymopapain is a protein consisting of 218 amino acids whose structure and properties closely resemble those of papain. Chymopapain, currently available lyophilized, is injected into the intervertebral disc in order to cleave the proteoglycans to treat sciatica due to herniated lumbar disc when it resists other medical treatments. Papain, alone or in combination, is used to treat digestive gastric or duodenal insufficiency such as postprandial disorders or bloating (Digestozym® ). Externally, it is used to treat mouth infection (Lysopain® ) and peripheral venous disorders (Tromshin® ), soothe inflammation (Panafil-White® ), heal wounds, and to kill germs. The anthelmintic property of the latex of Carica papaya L. is confirmed experimentally. Administration of a water suspension (2 g/Kg–8 g/Kg) of Carica papaya L. reduces by 55.5%–84.5% the number of Heligmosomoides polygyrus nematodes in necropsied Balb/c mice (Satrija F et al., 1995). The plant abrogates the survival of Haemonchus contortus cultured in vitro (Hounzangbe-Adote MS et al., 2005).

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Antimicrobial properties: The ability of Carica papaya L. to inhibit the proliferation of Candida albicans in vitro (Giordani R et al., 1996) is potentiated with fluconazole (Giordani R et al., 1997). Papain taken per os reduces herpes Simplex Virus infection as efficiently as aciclovir (Zovirax® ); (Kleine MW et al., 1995). Note that the leaves of Carica papaya L. contain carpaine, a piperidine alkaloid which reduces cardiac activity and annihilates amoeba. References

O

O N H

H N O

O

Carpaine

Giordani R, et al. (1996) Mycosis 39(3–4): 103–110. Giordani R, et al. (1997) Mycosis 40(11–12): 429–437. Holsinger JW, et al. (1968) J Am Med Ass 204, 734. Hounzangbe-Adote MS, et al. (2005) Research in Veterinary Science (78)2: 155–160. Kleine MW, et al. (1995) Phytomed 2(1): 7–15. Lohiya NK, et al. (1992) Int J Pharmacog 3(4): 32–38. Satrija F, et al. (1995) J Ethopharmacol 48(3): 161–164. Schmidt H (1995) Reprod Tox 9(1): 49–55. Udoh P, et al. (1999) Phytother Res 13(3): 226–228.

Warning: In high doses, papain is lethal. Death from hemorrhage following extensive destruction of the esophageal wall and the descending thoracic aorta resulted from the use of a papain suspension (1.2 g of papain over 12 hours period) to treat an obstruction caused by impacted meat (Holsinger JW et al., 1968). The effect of the latex of Carica papaya L. on pregnancy is still a subject of controversy. A number of experiments conducted in animals in the seventies demonstrated that the latex of Carica papaya L. abrogated a pregnancy, but a standardized papain (800 mg/Kg) given per os to Wistar rats (800 mg/Kg) during blastogenesis (day 0–day 6) or embryogenesis (day 6–day 15) did not show any anti-implantation properties nor embryonic toxicity (Schmidt H., 1995). Induction of the reversible antifertility with crude ethanolic extract of the seeds of Carica papaya L. in albino male rats was however observed (Lohiya NK et al., 1992). The same rats fed with 100 mg of the seeds of Carica papaya per kilogram of body weight developed degeneration of geminal epithelium, germ cells, and Leydig cells (Udoh P et al., 1999).

5. Family CUCURBITACEAE A. L. de Jussieu 1789 nom. conserv., the Cucumber family Physical description: The family Cucurbitaceae consists of about 90 genera and 700 species of tendriliferous and succulent climbers often abounding with

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oxygenated 5 -and 7 -steroids (cucurbitacins), piperidine alkaloids and pentacyclic triterpenoid saponins. The leaves are simple, alternate and without stipules. The blade is often palmately lobed, rugose, and the petiole includes a crescent or ring of asymmetrical vascular bundles. The flowers are axillary, showy, unisexual and actinomorphic. The calyx is tubular, and the corolla is tubular or comprises of free petals. The andrecium consists of several stamens which are free or variously united, and 1 anther which is always single-celled. The gynecium consists of 3 carpels united to form a compound, unilocular inferior ovary containing several ovules attached to parietal placentas. The style is simple. The fruits are berries, often large and palatable, or capsules containing several flattened seeds without endosperm and often containing ribosome inactivating proteins which might hold pharmaceutical potential. Pharmaceutical interest: Classical OCOCH3 examples of Cucurbitaceae are Cucumis sativus L. (cucumber), HO Cucumis melo L. (melon) and Citrulus lanatus (Thunb.) Mansf. (WaterO O melon). Cucurbitaceae have attracted H H OH a great deal of interest on account HO of the production of cucurbitacins which are highly toxic (LD50 : 1 mg/Kg O in mice by intraperitonneal injection), and imparted to the plants that conCucurbitacin E (elaterin) tain them bitterness, and drastic laxative and emetic properties. Examples of laxative drugs from Cucurbitaceae are Bryonia cretica L. subsp. dioica (Jacq.) Tutin (bryony), the dried pulp of Citrullus colocynthis (L.) Schrad. (bitter gourd) (Colocynth, British Pharmaceutical Codex, 1963) and the dried sediment which deposits in the juice of Ecballium elaterium (L.) A. Rich. (wild cucumber, squirting cucumber) (Elaterium, British Pharmaceutical Codex, 1934). The fresh seeds of Cucurbita pepo L. (pumpkin) (Cucurbita, British Pharmaceutical Codex, 1934) and Cucurbita maxima have long been used to expel intestinal worms. The oil expressed from the seeds has been used to treat benign prostate hypertrophy. Besides purgative properties, cucurbitacins are interesting because they exhibit a characteristic pattern of differential cytotoxicity, predominantly toward renal and brain tumors,

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and melanoma, and are therefore worth exploring further. Cucurbitacin E (elaterin), the active principle of Ecballium elaterium (L.) A. Rich., annihilates efficiently the survival of prostate carcinoma cells cultured in vitro (IC50 : 7 nM– 50 nM in 2–to 6–day exposures). The cytotoxicity of cucurbitacins is related to their ability to disrupt the F-actin cytoskeleton and thereby the division of cells. Note that Cucurbitaceae are also interesting for the proteins they contain in their roots and seeds. These proteins are abortifacient, antitumoral, ribosome inactivating, anti-HIV and immunomodulatory. It will be interesting to learn whether more intensive future research on Cucurbitaceae will disclose any molecules of chemotherapeutic interest. About 50 Cucurbitaceae plant species are medicinal in the Asia-Pacific, mostly on account of their steroidal and triterpenes contents. The fruits are mainly used to promote urination, soothe inflamed parts, check hemorrhages, counteract poisoning, treat fever diabetes, jaundice, and scabies, expel intestinal worms and to alleviate anxiety. Benincasa hispida (Thunb.) Cogn. [After Count Giuseppe Benincasa, a 16th century Italian botanist who founded the Botanic Garden at Pisa, and from Latin, hispidus = bristly] Synonymy: Benincasa cerifera Savi. Common names: Ash pumpkin, tallow gourd; kyaukpayon (Burmese); tung kua (Chinese); tougan (Japaneae); terak bileng, terak sayak, lepo ga (Malaysia); abobora de agua (Portuguese); bi dao (Cambodia, Laos, Vietnamese); suphala (Sanskrit); pushini (Tamil).

Physical description: It is a climber native to tropical Asia which is cultivated mainly in warm countries. The plant has a musky smell. The stems are angular, 3 mm–4 mm in diameter and hispid. Leaves: simple, alternate and without stipules. The petiole is 6 cm–8 cm × 2 mm and hispid. The blade is palmately 5-lobed, very thin, and hispid underneath. The blade is serrate, and shows 5–6 pairs of

Fig. 111. Benincasa hispida (Thunb.) Cogn.

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secondary nerves. The flowers are simple, axillary and showy. The flower pedicels are 5 cm–10 cm long and hispid. The calyx consists of 5 linear, 8 mm long hispid sepals. The corolla consists of 5 yellow, orbicular, very thin and showily nerved petals. The fruits are massive, 40 cm long, ovate berries covered with a dense chalky white powder (Fig. 111). Pharmaceutical interest: Antidiabetes properties: In regard to the antidiabetic property of Benincasa hispida (Thunb.) Cogn., a number of experiments conducted in vivo tend to demonstrate that the plant is inactive. An ethanolic extract of Benincasa hispida (Thunb.) administered at a dose of 250 mg/Kg orally to rats failed to lower blood sugar or to depress the peak value, after glucose load (Chandrasekar B et al., 1989). Central nervous properties: The quieting effect of Benincasa hispida (Thunb.) Cogn., which is probably mediated by some triterpenes or steroids, is not confirmed yet but Grover et al., (2000), show that the fresh fruit juice of Benincasa hispida (Thunb.) Cogn. assuages symptoms of morphine withdrawal, such as the jumping response and diarrhea. It will be interesting to learn whether further research on neuroactive principles from Benincasa hispida (Thunb.) Cogn. and Cucurbitaceae in general, will disclose any molecule of therapeutic interest. Properties on the immune system: The anti-inflammatory property of Benincasa hispida (Thunb.) Cogn. is confirmed experimentally and attributed to triterpenes. Alnusenol and multiflorenol, isolated from a methanolic extract of fruits of Benincasa hispida (Thunb.) Cogn. inhibit the release

Uses: In China, the fruits of Benincasa hispida (Thunb.) Cogn. are eaten to treat diabetes, dropsy and kidney diseases. The seeds are eaten to promote urination, relieve the bowels of costiveness, treat fever, heal hemorrhoids, and soothe inflamed intestines. The rind is eaten to promote urination and to invigorate the spleen. The pulp is used to promote urination, treat fever and as a demulcent. In India, the fruits are eaten to relieve the bowels of costiveness, promote urination and libido, check hemorrhages, treat strangury and expel urinary stones. The oil expressed from the seeds is soporific. In Indonesia, the fruits are eaten to invigorate health and to check hemorrhages. In Malaysia, the leaves are applied to bruises and a decoction of the fruit is drunk to combat hystero-epilepsy. In the Philippines, the fruits are eaten to treat disorders of the respiratory organs and applied to inflamed eyes.

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of histamine from rat exudate cells induced by antigen-antibody reaction (Yoshizumi S et al., 1998). In addition, a heteropolymer consisting of uronic acid, neutral sugars, protein, and phosphorus characterized from the hot water extract of the seeds of Benincasa hispida (Thunb.) Cogn. stimulates in vitro the development of peritoneal macrophages into antitumoral macrophages, and extend the survival period of mice bearing Meth A fibrosarcoma (Kamazawa Y et al., 1985). References Chandrasekar B, et al. (1989) Indian J Med Res 90: 300–305. Kamazawa Y, et al. (1985) Cancer Immunology, Immunotherapy 19(2): 79–84. Grovers JK, et al. (2000) Fitoter 71(6): 707–709. Yoshizumi S, et al. (1998) Yakugaku Zasshi 118(5): 188–192.

Warning: Caution must be taken as the toxic effects of this plant are unknown. Citrullus lanatus (Thunb.) Matsum. & Nak. [From Latin, citrullus = diminutive of citrus, and lana = wool] Synonymy: Citrullus vulgaris Schrad. Common names: Watermelon; paye (Burma); hsi kua (Chinese); pasteque (French); au lek (Cambodia, Laos, Vietnam); melao da India (Portuguese); chitra (Sanskrit); melon de agua (Spanish); cocomero (Italian).

Physical description: It is an annual, woolly climber native to Africa which is cultivated in several warm countries for its edible fruits. Leaves: simple, spiral and without stipules.The petiole is pilose, 2.1 cm–5.7 cm long, thin, and sheathing at the base. The tendrils are axillary and bifid. The blade is deeply incised, rigid, woolly on both surfaces, and laxly serrate. The blade shows 3–5 pairs of secondary nerves which are flat above and slightly raised below. The flowers are 1 cm × 7 mm, axillary and solitary. The calyx consists of 5 lobes which are narrowly lanceolate and equal in length to the corolla. The corolla is yellow within and greenish outside, and the lobes are ovate-oblong and 5-nerved.The flower pedicels are 1 cm–1.8 cm long, slender, and woolly. The fruits are smooth, globose, greenish berries, measuring up to 40 cm in diameter. The flesh is reddish-pink, or white, juicy and palatable. The seeds are blackish, marginated and glossy (Fig. 112).

Subclass Dilleniidae Uses: In China, the pulp and the rind are eaten to treat diabetes and jaundice, and to expel impurities. The pulp is used to soothe an inflamed throat, heal sores in the mouth and to fight dependence on alcohol. In India, the unripe fruits are used to strengthen, promote libido and to treat jaundice and fever. The seeds are used to promote libido, and the leaves are used to check bleeding. In Indonesia, the fruits are used to assuage rheumatic pains. In Malaysia, the juice of the roots is used to check bleeding after an abortion. In Palau, the fruits are used to treat beriberi and cystitis. In Cambodia, Laos, and Vietnam, the pulp and rind are eaten to regulate motion.

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Fig. 112. Citrullus lanatus (Thunb.) Mansf. From: KLU 040742. Flora of the Northern Mariana Islands. Ex. University of Guam Herbarium. Field collector: C. Bjork, 14 May 1985. Geographical localization: cultivated in farmers fields between Agric. Station and Maqpo. Botanical identification: de Wilde, 1996.

Pharmaceutical interest: To date, there are no recent studies on the possible pharmacological properties of Citrullus lanatus (Thunb.) Mansf. Some muscular and cardiovascular effects of α-elaterin-2-D-glucopyranoside isolated from Citrullus colocynthis (L.) Schrad. have been reported by Banerjee et al. (1976). References Banerjee SP, et al. (1976) J Pharm Sci 56(12): 1665–1667. Cantor DS, et al. (1987) Gastrointestinal Endoscopy 38(6): 734–735. Khanna SK, et al. (1992) Gastrointestinal Endoscopy 33(2): 129.

Warning: A number of studies indicate that colon cancers can be induced by excessive consumption of Citrullus lanatus (Thunb.) Mansf. (Cantor DS et al., 1987; Khanna SK et al., 1992). Lagenaria siceraria (Mol.) Standl. [From Latin, lagenaria = shaped like a bottle and from Hebrew, shekar = strong fermented drink] Physical description: It is a climber cultivated for its fruits which have manifold uses in the tropical regions. The plant has the greasy smell of a mild

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Synonymy: Lagenaria vulgaris Ser., Lagenaria leucantha Rusby. Common names: Bottle gourd; gourde de pelerin ´ (French); businswai (Burma); hu lu (Chinese); urong ka’ dai, lepo ga’; (Kenyah); cabaceira (Portuguese); alabu (Sanskrit); calabeza vinatera (Spanish); shorakkai (Tamil).

stink bug. The stems are smooth, hairy, and 5-angled. Leaves: simple, alternate and without stipules. The petiole is hairy and 3.4 cm × 1.3 cm– 1 mm. The tendrils are hairy, bifid, and 3.3 cm–4.5 cm long. The blade is papery, hairy, somewhat 5-lobed, Fig. 113. Lagenaria siceraria (Mol.) Standl. laxly serrate, and shows 2–3 pairs of From: KLU Herbarium 28830. Flora of Sarawak. secondary nerves which are slightly Field collector: Chin See Chun, 26 Feb 1977. raised on both surfaces. The flow- Geographical localization: farm of Tua1 Kampong opposite Sungei Uket Bio’ about 4 2 miles ers are axillary, solitary, monoecious up river from Long Selatong Ulu. Botanical or dioecious. The flower pedicel is identification: de Wilde 1996. 8.2 cm × 1 mm and hairy. The calyx is conical, 2 cm long and produces 5 linear sepals. The corolla is showy, whitish, and consists of 5 orbiculate and very thin 3 cm long petals. The andrecium consists of 3 stamens which are connate and included. The ovary is oblong and pubescent and encloses several ovules which are attached to parietal placentas, the style is short and produces upward 3-bifid stigmatic lobes. Uses: In China, Cambodia, Laos and The fruits are 30 cm long, flask-shaped Vietnam, the pulp of Lagenaria sicerberries with a 20 cm long neck. The aria (Mol.) Standl. is used to treat seeds are numerous, 1.6 cm–2 cm, fever, promote urination, and relieve white, compressed, and with marginal the bowels of costiveness. In Malaysia, grooves. Although bitter, the young the pulp is eaten to treat colic and to fruits, flowers and shoots are eaten. counteract the putrefaction of the skin. Fruits that have ripen are used to make In Indonesia, the juice squeezed from floats, bottles and ladles (Fig. 113). the young fruit is drunk to treat fever. Pharmaceutical interest: Lagenin: Lagenaria siceraria (Mol.) Standl. is known to contain a 20 KDa ribosome inactivating protein called

In the Philippines, the green fruits are used to treat diseases of the breast or chest. The pulp is used to counteract poisoning, assuage cough and treat fever.

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lagenin, which inhibits cell-free translation in rabbit reticulocyte system with an IC50 value of 0.21 nM. Lagenin exerts ribonuclease activity on yeast tRNA with an activity of 45 U/mg (Wang HX et al, 2000). Dietetic properties: A diet containing 5%, 10%, or 20% of Lagenaria siceraria (Mol.) Standl. lowers to 24% the incidence of 1,2-dimethylhydrazine-induced colonic carcinogenesis in mice (Furukawa K et al., 1995). References Furukawa K, et al. (1995) Cancer 1508–1515. Wang HX, et al. (2000) Life Sci 67(21): 2631–2638.

Warning: Caution must be taken as the toxic effects of this plant are unknown. Luffa acutangula Roxb. [From Arabic, lufah = Luffa acutangula Roxb., and from Latin, acutus = acute and angulus = angle]

Common names: Thapwot (Burmese); ronung chrung (Cambodian); jalini (Sanskrit); pekankai (Tamil).

Physical description: It is a monoecious climber cultivated in many warm countries for its edible berries. The stems are 5-angled, hairy and rigid. Leaves: simple, alternate and without stipules. The petiole is channeled, hairy and 7 mm– 2 cm long. The tendrils are slender and 3-fid. The blade is papery, 5-lobed, 5 cm × 6 cm–7 cm × 8.5 cm, and mottled with white spots on the surface and hairy underneath. The nerves are flat above and raised on the underside of the blade and the tertiary nerves are indistinct. The male flowers are arranged in axillary, 12–20 flowered racemes of 10 cm–15 cm long. The calyx is hairy, 1.3 cm long and consists of lanceolate 1 cm long sepals. The corolla comprises of 5 petals of 2 cm long, and is somewhat hairy, obovate, and yellow with green veins. The andrecium consists of 3 stamens. The female flowers are solitary, in the same axil as the males on 5 cm–10 cm long pedicels and comprise of an ovary which is strongly ribbed. The fruits are smooth, 10-ribbed, green, about 15 cm × 4 cm dull green berries (Fig. 114).

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Uses: In Cambodia, Laos and Vietnam, the seeds are eaten to induce vomiting, stop hiccups, and relieve the bowels of costiveness. A paste made from the leaves is used to treat zona. In India, the berries are used to treat fever, expel worms from intestines, and cure biliousness, asthma, and bronchitis. In Indonesia, the leaves are used to treat fever. In Malaysia, the juice is used after childbirth.

Fig. 114. Luffa acutangula Roxb. From: KLU Herbarium 041871. Flora of Malaya. Field collector: Rohani Bte Hassan, 21 Aug 1990. Geographical localization: Kampung Paloh, Kelantan, “Tanah Pamah”. Botanical identification: de Wilde 1996.

Pharmaceutical interest: Luffaculin:The seeds of Luffa acutangula Roxb. contain a ribosome inactivating protein, luffaculin, which is abortifacient, antitumor, and immunomodulatory (Ng TB et al., 1992). The seeds are also known to contain cucurbitacins B and a number of oleanane-type triterpenes saponins (Barua AK et al., 1958; Nagao T et al., 1991). References Barua AK, et al. (1958) J Indian Chem Soc 35: 480–482. Nagao T, et al. (1991) Chem Pharm Bull 39(3): 599–606. Ng TB, et al. (1992) General Pharmacology 23(4): 579–590.

Warning: Caution must be taken as the toxic effects of this plant are unknown. Momordica charantia L. [From Latin, mordere ¯ = bite] Physical description: It is a slender annual climber cultivated in the tropical regions for its edible berries. The stems are hairy and 1 mm–2 mm in

Subclass Dilleniidae

diameter. Leaves: simple, alternate and without stipules. The petiole is 1 cm–2 cm long and hairy. The tendrils are opposite the leaves, and 1 cm– 6 cm long. The blade is very thin, mottled with very small blackish spots below, hairy, 3.4 cm × 3.5 cm–2.9 cm × 3.7 cm and deeply 5–7-lobed. The nerves are sunken above, flat below and hairy. The margin is laxly toothed. The flowers are axillary, solitary, yellow and attached to 4 cm–10 cm long pedicels where small bracts are found at or below the middle. The calyx is campanulate, 5-lobed, hairy and 8 mm–10 mm long.The calyx lobes are 5 mm–6 mm long, elliptic and acute. The corolla is irregular and yellowish and consists of 5, 1.6 cm–3 cm long petals which are free, showily veined, hairy and rotate. The andrecium comprises of 3 stamens which are conduplicate. The ovary is fusiform and muricate, and develops upwards into a 3-fid stigma. The fruits are edible, fusiform, muricate, bright orange when ripe, 5 cm–15 cm long, and cucumber-shaped berries containing several seeds. The seeds are 8 mm– 13 mm long, compressed, corrugated on the margin, sculptured on both surfaces and embedded in a crimson aril (Fig. 115).

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Synonymy: Momordica balsamina sensu Blanco. Common names: Wild basalm apple, bitter gourd, carilla fruit; kyethenka (Burma); mreas (Cambodian); koo kwa kan (Chinese); pandipane (French); periah (Malay); pepino de Sao˜ Gregorio (Portuguese); karaka; patu (Sanskrit); pakal (Tamil); kho qua (Vietnamese). Uses: In China, the fruits of Momordica charantia L. are eaten to reduce body temperature, invigorate health, relieve the bowels of costiveness and stop flatulence. In Cambodia, the leaves are used to combat fever and delirium. In Indonesia, a decoction of the leaves is drunk to relieve the bowels of costiveness, treat liver diseases and expel intestinal worms. In India, the fruits are eaten to relieve the bowels of costiveness and expel intestinal worms. In Malaysia, the fruits are used to treat diabetes, and a poultice of the powdered leaves is applied to burns. A decoction of Momordica charantia L. is drunk to abort a pregnancy. In the Philippines, the juice expressed from the green fruit is drunk to treat chronic colitis and dysentery. In Cambodia, Laos and Vietnam, the cooked fruit is used to stop catarrh, flux and cough.

Pharmaceutical potential: Antidiabetes properties: In regard to the antidiabetes properties of Momordica charantia L., a number of experiments conducted in vivo tend to demonstrate that intake of the fruits improves glucose tolerance. An extract of the fruit given for ten weeks lowers glycaemia in streptozocin-induced type I diabetic rats (Ahmed I et al., 2001). The juice expressed from the fruit improves significantly the glucose tolerance of diabetic patients (Welihinda J et al., 1986). The precise mechanism of action involved here is unknown but one could set the

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Fig. 115. Momordica charantia L. From: Delhi University Herbarium 004378. Field collector: PS Sabharwal, 8 Sep 1957. Altitude 500 ft. Geographical localization: Najafgarh, Delhi. Botanical identification: de Wilde 1996.

hypothesis that the hypoglycaemic property would not result from an insulinmediated mechanism (Sarkar S et al., 1996; Madsuda H et al., 1997), but from a glucocorticoid-mediated by oleanolic acid saponins. Being structurally close to glucocorticoids, the triterpenes of Momordica charantia L. have the tendency to occupy glucocorticoid receptors and act thereby as glucocorticoid antagonist in two instances, hypoglycaemia and abortion. An example of glucocorticoid antagonist used in therapeutic is RU486 which causes abortion and eliminates carbohydrate intolerance in many subjects (Mantero F et al., 1989). Another hypothesis is that, given per os, the triterpenes of Momordica charantia L. suppress the transfer of glucose from the stomach to the small intestine by inhibiting glucose transport at the brush border of the small intestine, as demonstrated with momordin Ic (Matsuda H et al., 1998a). Other steroidal properties: Oleanolic acid 3-O-monodesmoside characterized from Momordica cochinchinensis Spreng. exhibits antipruritic properties in mice (Matsuda H et al., 1998). Petroleum ether, benzenic and alcohol extracts of the seeds of Momordica charantia L. given to rats at a dose

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of 25 mg/100 g/day for 35 days, reduce the number of spermatocytes, spermatids and spermatozoa. The alcohol extract is more potent in its antispermatogen, antisteroidogen and androgen properties (Naseem MZ et al., 1998).

COOH HOOC HO HO HO

O

O

O O OH

OH Momordin I

Cytotoxic properties: Momordica charantia L. has attracted a great deal of interest on account of a series of oleanolic acid saponins known as momordin. Momordin are anticarcinogenic in rodents through the enzymes of biotransformation and detoxification (Ganguly C et al., 2000). Oleanolic acid momordin I, Id and Ie reduce in vitro the Jun/Fos-DNA interaction which is a crucial factor in transmitting tumor-promoting signals from the extracellular environment to nuclear transmission machinery (Lee DK et al., 1998). Topical application of an extract of peels of the fruits of Momordica charantia L. (100 µg/animal/day) reduces the proliferation of 7, 12-dimethylbenz-[a]-anthracene-induced skin papilloma in mice (Singh A et al., 1998). Antimutagen principles characterized from the green fruit are identified as 3-O-[6 -O-palmitoyl-β-D-glucosylstigmasta-5,25(27)-dien and its stearyl derivative. At a dosage range of 50.5 µg extract/g-12.5 µg extract/g in mice, the mixture reduces by about 80% the number of micronucleated polychromatic erythrocytes caused by mitomycin C. Structure-activity correlation studies suggest that the antimutagen property may reside in the peculiar lipid-like structure of the acylglucosylsterols. Ingestion of these compounds may result in their absorption in the plasma membrane lipid bilayer which would adversely affect the membrane permeability towards mitomycin C and disrupt the cellular property of the latter (Guevara AP et al., 1990). Antimicrobial properties: An extract of Momordica charantia L. inhibits the growth of Mycobacterium tuberculosis cultured in vitro (France AP et al., 1998). The fruit of Momordica charantia L. contains a protein which inhibits, the enzymatic activity of HIV-1 reverse transcriptase in vitro (Jiratchariyakul W et al., 2001).

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References Ahmed I, et al. (2001) Diabetes Res Clin Pract 51(3): 155–161. Chan WY, et al. (1986) Contraception 34(5): 537–544. France AP, et al. (1998) PR Health Sc J 17(3): 243–252. Ganguly C, et al. (2000) Eur J Cancer Prev 9(4): 283–288. Guevara AP, et al. (1990) Mutat-Res Jun: 230(2): 121–126. Jiratchariyakul W, et al. (2001) Planta Med 67(4): 350–353. Lee DK, et al. (1998) Anticancer Res 18(1A): 119–124. Matsuda H, et al. (1997) Biol Pharm Bull 20(6): 717–719. Madsuda H, et al. (1998) Biol Pharm Bull 21(11): 1231–1233. Matsuda H, et al. (1998a) Chem Pharm Bull Tokyo 46(9): 1399–1403. Mantero F, et al. (1989) The adrenal and hypertension: from cloning to clinic. New York: Raven Press: 273–284. Naseem MZ, et al. (1998) J Ethnopharmacol 61(1): 9–16. Ramos Ruiz A, et al. (1996) J Ethnopharmacol 52(3): 123–127. Sarkar S, et al. (1996) Pharmacol Res 33(1): 1–4. Singh A, et al. (1998) Toxicol Lett 94(1): 37–46. Welihinda J, et al. (1986) J Ethnopharmacol 17(3): 277–282.

Warning: The seeds of Momordica charantia L. must not be consumed during the early stage of pregnancy because they contain some proteins called momorcharins, which are teratogenic to the cultured mouse embryos at the early organogenesis stage (Chan WY et al., 1986). An aqueous extract of Momordica charantia L. causes a statistical significant genotoxic effect in the plate incorporation assay using Aspergillus ridulans (Ramos Ruz A et al., 1996). Momordica cochinchinensis (Lour.) Spreng. [From Latin, mordere ¯ = bite and cochinchinensis = from Cochinchina] Physical description: It is a dioecious, Common names: Samongnway stout and perennial climber which grows (Burma); mu pieh tzu, fan muh pee in India, Southeast Asia and China. The (Chinese); day gae (Vietnamese); stems are pilose at the apex and rugose. karka (Sanskrit). Leaves: simple, alternate and without stipules. The petiole is 1.5 cm–2.7 cm long and thin, pilose at first, somewhat twisted, and channeled. The blade is cordate, leathery, 6 cm–12 cm × 7 cm– 9 cm and molted with numerous microscopic 2–5-lobed bodies underneath. The margin is recurved and laxly toothed. The blade shows 4–8 pairs of secondary nerves. The tertiary nerves are scalariform, and the midrib is raised on both surfaces of the blade.The tendrils are axillary, spring-shaped and 4.5 cm– 12 cm long. The inflorescences are axillary and solitary. The flower pedicels are 2.5 cm–15 cm long, angularly furrowed and pilose. The calyx is pilose, 5-lobed, 1.3 cm–1.6 cm long, and the sepals are oblong, lanceolate and acute.

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The corolla is white, tinged with yellow, and consists of 5, 5.7 cm × 2.5 cm, obovate and oblong petals. The fruits are 4 cm–10 cm in diameter, globose, spiny red berries. The seeds are compressed and ovoid (Fig. 116). Uses: In Burma, the seeds of Momordica cochinchinensis (Lour.) Spreng. are eaten to assuage chest pain. In China, the seeds are eaten to treat fluxes, liver diseases, hemorrhoids, breast cancer and malaria, and to heal wounds and ulcers. In Indonesia, the leaves are applied externally to swollen legs. In Laos, Cambodia and Vietnam, the seeds are used to counteract putrefaction of the skin. In the Philippines, the roots are used to produce soap.

Pharmaceutical interest:

Fig. 116. Momordica cochinchinensis (Lour.) Spreng. From: KLU Herbarium 039071. Flora of Sulawei Selatan. Field collector: SC Chin, 12 June 1986. Geographical localization: Maros, limestone Hills near Leangleang. Botanical identification: de Wide 1996.

Anti-inflammatory property: The antiinflammatory property of Momordica cochinchinensis (Lour.) Spreng. is confirmed experimentally: oleanolic acid saponins isolated from the roots of Momordica cochinchinensis (Lour.) Spreng. reduce pruritus induced in mice (Matsuda H et al., 1998). Antitumor properties: The roots of Momordica cochinchinensis (Lour.) Spreng. contain a series of saponins with hemolytic properties, as well as ribosome inactivating proteins (Ng TB et al., 1986; 1992). Momordin Id: 3β-{([O-β-D-xylopyranosyl-(1 → 2)-O-b-D-xylopyranosyl-(1 → 3)]-O-β-Dglucopyran-uronosyl)oxy}-olean-12-ene-28-oic acid is present in the root of this plant, hence it has antitumoral potential (Noriaki K et al., 1988). References Matsuda H, et al. (1998) Biol Pharm Bull 21(11): 1231–1233. Ng TB, et al. (1992) General Pharmacology 23(4): 579–590. Ng TB, et al. (1986) J Ethnopharmacol 18(1): 55–61. Noriaki K, et al. (1988) Phytochem 27(11): 3585–3591.

Warning: Caution must be taken as the toxic effects of this plant are unknown.

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Trichosanthes kirilowii Maxim. [From Greek, trikhos = hair and anthos = flower] Physical description: It is a climber found Common names: Chinese in Japan, Korea and China. The tendrils are cucumber, Chinese snakegourd, 2–5-fid. Leaves: simple, exstipulate and spigua-lou tian-hua-fen (Chinese). ral. The blade is broad ovate to orbiculate, remotely dentate or 3–7-lobed, cordate at the base, pilose and punctuate on both sides. The inflorescences are axillary 10 cm–20 cm long racemes. The bracts are obovate or ovate, and 2 cm–2.5 cm long. The flowers are ephemeral and dirty white. The corolla consists of 5 petals which are fringed at the apex. The fruits are oblong, 9 cm–10 cm, orange-yellow berries containing several ovate or oblong,1.1 cm–1.4 cm × 8 mm–9 mm light brown seeds. Pharmaceutical interest: Trichosanthin: Trichosanthes species Uses: In China and Taiwan, a are interesting because they produce decoction of the roots is drunk to a series of ribosome-inactivating proquench thirst, treat fever, and promote teins which might be of value in expectoration, urination and milk treating cancers and HIV. The roots secretion. In Korea, the roots are of Trichosanthes kirilowii Maxim. are used to promote expectoration, heal known, for instance, to contain trihemorrhoids and moisten dry skin. chosanthin, a 27 KDa single ribosomeinactivating protein consisting of 247 amino acids, which exhibits manifold pharmacological properties. Trichosantin is active against leukaemia (Takemoto DJ et al., 1998) and has been described by some as a “promising anti-Human Immunodeficiency Virus”. Trichosanthin annihilates infected macrophages, and eliminate this major reservoir of Human Immunodeficiency Virus from the body. Since the discovery of its specific injurious properties on human placental trophoblasts in the 1970’s, trichosanthin has been used clinically in China to cause an abortion and to treat diseases of trophoblastic origin such as hydatiform mole, invasive mole and choriocarcinoma. Soon after the laboratory finding in 1989 by McGrath et al., that it inhibits the replication of HIV-1 in both acutely infected T-lymphoblastoid cells and in chronically-infected macrophages, and selectively kills HIV-infected cells while leaving uninfected cells unharmed, clinical trials of trichosanthin as a potential treatment for HIV have been carried out in the States. Trichosanthin attacks the life cycle of the virus at an entirely different point from zidovudine (AZT® ) and related drugs, and in other words, it has a unique mechanism of action complementary to other drugs. Clinical reports show that trichosanthin has some levels of properties on HIV patients and it has been suggested as a possible treatment that may fill the gap in the treatment of the Human Immunodeficiency Virus infection. Other substances of

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interest are a series of multiflorane pentacyclic triterpenes which inhibit the early expression of Epstein-Barr Virus (EBV) antigen by Raji cells induced by 12-O-tetradecanoylphorbol-13-acetate (Akihisa T et al., 2001). Anti-tumor properties:The plant is known to elaborate trichomislin, a ribosomeinactivating protein, which induces apoptosis via mitochondria and the enzymatic activity of caspase-3 (Mi SL et al., 2005). References Akihisa T, et al. (2001) Cancer Lett 173(1): 9–14. McGrath MS, et al. (1989) Proceedings of the National Academy of Sciences, USA, April 15, 1989. Takemoto DJ, et al. (1998) Anticancer Res 18(1A): 357–361. Mi SL, et al. (2005) Archives of Biochemistry and Biophysics (43)2, 15: 258–265.

Warning: Side effects of trichosanthin observed during clinical trials include allergic reactions, neurotoxic effect and flu-like symptoms. Among them, the most dangerous complication seen with the drug is anaphylactic shock, a sudden, severe life-threatening allergic reaction that can kill within days. This reaction was experienced by 10–20 percent of people using the drug. Therefore, it is critical to modify the molecular structure of trichosanthin in order to decrease its side effects.

6. Family DATISCACEAE Lindley 1830 nom. conserv., the Datisca Family Physical description: The family Datiscaceae is a little family of 3 genera and 4 species of Asian perennial herbs and trees known to produce flavonoids. In this family, the leaves are simple or compound, alternate and without stipules. The flowers are unisexual. The male flowers comprise of a calyx of 4–8, free or united sepals in a lobed tube, a corolla of 0–8 petals, an andrecium of up to 25 stamens with tetrasporangiate anthers opening by longitudinal slits and dithecal. The female flowers comO prise of a calyx of 3–8 sepals, and a O gynecium of 3–8 carpels united to form a compound, unilocular, inferior ovary containOH O ing anatropous ovules attached to parietal placentas. The fruits are capsular, open apically between the persistent styles and conOH tain several numerous, very small seeds with straight, cylindrical, oily and dicotyledonous O embryos. O Pharmaceutical interest: It will be interesting to learn whether more intensive future

O

Datiscacin

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research on this family will disclose any molecules of pharmaceutical interest such as cucurbitacins (datiscacin). Octomeles sumatrana Miq. and Tetrameles nudiflora R. Br. are used in the Asia-Pacific to treat abdominal disorders. Octomeles sumatrana Miq. [From Latin, octomele = eight partite and sumatrana = from Sumatra] Synonymy: Octomeles moluccana Teisjm. & Binnend. ex Hassk. Common names: Erima, binuang (Malay); benuang (Indonesian); limo (Papua New Guinea).

Uses: In Indonesia, the sap expressed from the young leaves of Octomeles sumatrana Miq. is used to assuage abdominal pain. In the Philippines, a decoction of the bark is drunk to invigorate health. The pharmacological potential of Octomeles sumatrana Miq. remains unexplored.

Physical description: It is a timber tree found in Malaysia and Indonesia. The stems are smooth, glabrous and terete. Leaves: simple, spiral and without stipules. The petiole is quadrangular and 12.5 cm– 10 cm × 3 mm–4 mm. The blade is ovate, glabrous, broadly ellipticcordate, leathery, and 18.5 cm– 19 cm × 13.5 cm–15 cm and wavy at the margin. The nervations are sunken above and raised below the blade, showing 7–9 pairs of secondary nerves and a few scalariform tertiary nerves. The inflorescences are long and terminal spikes. The fruits are dehiscent capsules containing many seeds and marked at Fig. 117. Octomeles sumatrana Miq. From: KLU the apex with a vestigial calyx tube Herbarium 17557. Flora of Sabah. Botanical identification.: PS Ashton, March 1973. (Fig. 117).

7. Family BEGONIACEAE C. A. Agardh 1825, nom. conserv., the Begonia Family Physical description: The family Begoniaceae consists principally of the large tropical genus Begonia, which consists of about 1000 species of succulent, sappy herbs and soft-stemmed shrubs. Begoniaceae are known to produce cucurbitacins, and oxalic acid. The leaves in this family are simple,

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203

alternate, principally palmately veined and often palmately lobed, and toothed, and have large stipules. The flowers are unisexual and irregular, and arranged in axillary, cymose, occasionally long-pedunculate inflorescences. The perianth consists of up to 10 petaloid tepals. The andrecium comprises of 4 or more stamens originating in a centripetal sequence. The gynecium consists of 3 carpels forming a compound, inferior, plurilocular ovary containing several ovules attached to axillary placentas and developing upwards into a distinct style. The fruits are loculicidal capsules, or berries containing several small seeds. The structures of the andrecium and gynecium in the family Begoniaceae are unusual for members of the Violales. However, one could say that cucurbitacins justify the classification of Begoniaceae with the Cucurbitaceae and Datiscaceae in the order Violales, or at least their common ViolalesMalvales ancestors. Pharmaceutical interest: Many plants classified within the genera Begonia are cultivated to decorate gardens. Begoniaceae are interesting because they contain cucurbitacins which hold potential for the treatment of cancer (see p.). Begonia evansia Andr. (Begonia discolor Ait.), Begonia fimbristipulata Hance, Begonia isoptera Dryand. and Begonia oblonga Merr. are of medicinal value in the Asia-Pacific. Most of these herbs are used as a counter-irritant on account of the oxalic acid. Begonia species [From Michel Begon, a French administrator of Louis XIV King of France] Physical description:The leaves of Begonia species are succulent, alternate, distichous, long-petiolate, stipulate, simple and cauline or from rhizomes. The blade is cordate at the base and very asymmetrical. The margin is toothed or lobed. The flowers are monoecious, in clusters of axillary cymes. The male flowers are actinomorphic or not, showy, pink, white or reddish. The perianth comprises of 4 tepals, the pair of outer ones large and petal-like.The andrecium comprises of several 2-celled and basixified stamens forming a dense capitulum.The female flowers comprise of as many 2-lobed or branched styles as the locules. The stigmas are prominent, and the placentation in the ovary is axillary. The fruits are loculicidal or irregularly dehiscent asymmetrical 3-winged capsules containing several seeds which are very small. Pharmaceutical potential: A number of plants classified within the genus Begonia are counter-irritant. In Malaysia, Begonia isoptera Dryand. is pounded

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and applied externally to assuage the discomfort caused by an enlarged spleen. A handful of Begonia fimbristipulata Hance is boiled in water and the decoction is used to relieve cough, stop haemoptysis, and to treat fever and pneumonia. A paste made from the same plant is applied to swollen parts, sprains and burns. In Papua New Guinea, the sap expressed from the leaves of Begonia augustae Irmsch. is used as a counter-irritant remedy to soothe inflamed areas.The ashes of the leaves of several Begonia species are applied to the umbilical cord, and the leaves are heated and applied to the skin to assuage abdominal pain. In the Philippines, the leaves of Begonia oblonga Merr. are used to counteract the toxic effect of Dioscorea. In the Solomon islands, a decoction of the leaves of the Begonia species is used to assuage stomach discomfort. In Cambodia, Laos, and Vietnam, the roots of the Begonia species are used to promote urination and milk secretion, and to relieve the bowels of costiveness. Pharmaceutical interest:The counter-irritant property of the O O Begonia species is attributed to the crystals of oxalic acid OH which abound in the plant. Crystals of oxalic acid are sharp HO and irritate the mucosa and the epidermis. Begonia species Oxalic acid have attracted a great deal of interest on account of cucurbitacins (see p.). An extract of Begonia plejeba displays a characteristic pattern of differential cytotoxicity profile predominantly toward renal and brain tumors and melanoma in the NCI human disease-oriented screening panel.Further fractionations resulted in the characterization of cucurbitacin B (Fuller RW et al., 1994). HO

HO

O H

O

OR H

OH

O

Cucurbitacin B (R= Ac) Cucurbitacin D (R= H)

References Fuller RW, et al. (1994) J Nat Prod 57(10): 1442–1445. Paulsen E (1998) Contact Dermatitis 38(1): 14–19.

Warning: Occupational dermatitis among gardeners and greenhouse workers who come into contact with the Begonia species is not rare (Paulsen E, 1998).

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205

D. Order CAPPARALES Hutchinson 1926 The order Capparales consists of 5 families and nearly 4000 species of plants which are thought to have originated from the order Theales. By far, the largest family of the order Capparales is the family Brassicaceae which consists of about 3000 species of plants. Capparales are small trees, shrubs, climbers and herbs, the most characteristic chemical feature is the use of isothiocyanates as a chemical repellent. Isothiocyanates or mustard oils are liberated upon enzymatic hydrolysis of glucosinolates by an enzyme called myrosin. Isothiocyanates are interesting because they are cytotoxic, antimicrobial and irritating, hence the use of Capparales to make counter-irritant remedies.

1. Family CAPPARACEAE A. L. de Jussieu 1789 nom. conserv., the Caper Family Physical description: The family Capparaceae or Capparidaceae consists of about 45 genera and about 800 species of treelets, shrubs and herbs, which are principally xerophytic, pungent, tropical and subtropical, containing isothiocyanates (mustard oils), flavonoids, and occasionally pyrrolidine alkaloids. In this family, the leaves are alternate, opposite, simple or trifoliate or often palmately compound.The stipules are absent or very small.The flowers are bisexual, actinomorphic, hypogynous, axillary or terminal, solitary or in racemes. During plant collection, Capparales are easily recognizable by an elongated receptacle called gynophore or androgynophore. The calyx consists of 2–6 free, imbricate or valvate sepals, in 2 opposite, decussate pairs, or partially united, and distinct or connate below. The corolla comprises of up to 6 petals. The andrecium is often showy, and consists of several stamens initiated in a centrifugal sequence, with 2-celled and longitudinally dehiscent anthers. The gynecium consists of 2–12 carpels united to form a unilocular ovary which is sessile or supported by a long or short gynophore. The ovary encloses a few or many ovules attached to parietal placentas and develops upward into a single terminal style with a capitate or 2-lobed stigma. The fruits are pungent drupes or berries containing reniform or angular seeds. Pharmaceutical interest: An example of Capparaceae is Capparis spinosa, the buds of which (caper) are palatable. Glucosinolates are anionic glycosides responsible for the characteristic aroma of capers and the number of edible Brassicaceae

HO H

R

H O O

HO HO

H

S

OH H

H

Glucosinolate

N

SO3-

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(mustard, radish, and cabbage). Glucosinolates are suspected to be responsible for hypothyroidism, but their presence in the diet could have a protective effect against colon cancer. About 20 species of plants classified within the family Capparaceae are used medicinally in the Asia-Pacific. These are often used as counter-irritant remedies. Cleome gynandra L. [From Greek, kleome = Ancient name for a mustard-like plant and gunandros = of doubtful sex] Synonymy: Gynandropsis gynandra (L.) Briq., Gynandropsys pentaphylla DC. Common names: Cat’s whiskers, five-leaved cleome, bastard mustard; maman hantu (Malay); pai hua ts’ai (Chinese); man ma tia (Cambodia, Laos, Vietnamese); pissat de chien (French); cincocinco, silisihan (Filipino); ajagandha, kabani (Sanskrit); veali, kadugu (Tamil).

Uses: Cleome gynandra L. is a counter-irritant remedy. In China, the seeds are used to stop flatulence and a decoction of the plant is applied externally to treat piles and rheumatism. In Indonesia, the crushed leaves are applied externally to treat herpes, and the plant is used internally to promote expectoration and to stop flatulence. In Malaysia, the crushed leaves are applied externally to treat fever and rheumatism. A decoction of about 30 g of this plant is used to treat malaria, hepatitis, and leucorrhea. The seeds are eaten to prevent a malarial attack. In the Philippines, the leaves are eaten to treat bilious disorders. In Taiwan, a decoction of Cleome gynandra L. is drunk to treat gonorrhea and to stop dysentery. In Cambodia, Laos, and Vietnam, the roots are invigorating and antiscorbutic. The leaves are applied to the lumbar region to assuage pain in the loins. In India, half a teacup full of seeds given twice daily in a decoction, is eaten to treat convulsive infection, typhus, and fever. The leaves are used externally to heal boils.

Physical description: It is an annual and upright branched herb which grows to a height of 1.2 m. It is native to East and Southeast China. The stems and branches are striate and more or less clothed in white hairs. The leaves are 3–5 foliate. The petiole is 5 mm–7.6 mm long with occasionally small distant prickles. The leaflets are subsessile, 2 cm–4 cm × 1.2 cm– 2.5 cm, elliptic-obovate, obtuse, acute or acuminate, and pubescent on both sides. The margin is crenatedentate or subentire. The flowers are corymbose and elongating into dense bracteate racemes. The flower pedicels are 1.2 cm–2 cm long, viscid and pubescent. The bracts are subsessile, trifoliate, and have small obovate leaflets. The sepals are lanceolate, glandular, pubescent green and have white veins. The corolla comprises of 5 petals which are 1.5 cm long, broad,

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207

obovate, with a long narrow claw and light pink. The gynophore is 2 cm– 2.5 cm long. The stamens are purple and numerous. The ovary is linearoblong and glandular, and the style is very small. The fruits are 5 cm–9 cm × 4 cm–5 cm capsules, which are viscid, pubescent, obliquely striated, and containing several seeds which are muricate and dark brown (Fig. 118). Pharmaceutical interest: The counter-irritant property of Cleome gynandra L. is attributed to glucosinolates. When the leaves of any glucosinolatecontaining plant are bruised, glucosinolates are hydrolyzed by a β-thioglucosidase enzyme (myrosin) Fig. 118. Cleome gynandra L. into a number of extremely reactive, volatile and pungent isothiocyanates, which cause skin tingling and rubefaction, and upon prolonged contact with the skin vesication (Fig. 119). In addition, isothiocyanates capture iodide and prevent its uptake by the thyroid resulting in hypothyroidism and goiter. Isothiocyanates occur in Brassica nigra (L.) Koch. (family Brassicaceae), which has been used since ancient times to make cataplasms. The therapeutic potential of Cleome gynandra L. is open for pharmacological exploration. HO H

O S HO HO

H

OH H

R

R

H O

N

N

SO3-

C S

H

HO H

H O OH

HO HO

H

OH H

H

Fig. 119. Release of isothiocyanates from glucosinolates in Capparales.

Warning: Caution must be taken as the toxic effects of this plant are unknown.

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Cleome viscosa L. [From Greek, kleome = Ancient name for a mustard-like plant and from Latin, viscum = birdlime] Physical description: It is a tropical, annual, upright, smelly and bitter herb which grows to a height of 30 cm–90 cm. The stems are grooved, and densely clothed in glandular and simple hairs. Synonymy: Cleome icosandra L., PoliLeaves: 3–5 foliate. The petiole of nasia icosandra (L.) Wight. & Arn., the lower leaves is 2.5 cm–5 cm long Polanisia viscosa DC., Cleome cheliand becomes shorter upward.The folidonii sensu Burk. Dict. (fide Jacobs). oles are elliptic, oblong or obovate, Common names: Sticky cleome; acute or obtuse, and the terminal the herbe puante, brede ` puante (French); largest (4.3 cm × 2.5 cm). The petiadityabhakta, ´ ankakanta ´ (Sanskrit). olules are short and hairy. The flowers are yellow, axillary, and organized Uses: Cleome viscosa L. is a counterinto lax racemes. The flower pedicels irritant remedy. In Malaysia, Cleome are long and thin, terete, and hairy.The viscosa L. is used to stop flatusepals are oblong, lanceolate, 1.2 cm lence. A decoction is drunk to treat long and conspicuously veined. The intestinal discomfort, to stop diarrhea andrecium comprises of about 20 staand to expel intestinal worms. Extermens. The fruits are 5 cm–6.3 cm × nally, the plant is used to assuage headache and to treat rheumatism. In 4 mm, upright, hairy, obliquely striate the Philippines, Cleome viscosa L. is and subglobose capsules containing used to expel intestinal worms, and several seeds (Fig. 120).

Fig. 120. Cleome viscosa L.

maggots from ulcers. A paste of the powdered leaves is used to assuage headache. In Taiwan, the plant is used to treat rheumatism and to expel intestinal worms, while externally, it is used to treat inflamed ears. In Cambodia, Laos, and Vietnam, an infusion is used to counteract putrefaction and the roots are used to treat scurvy. The vapor obtained from steaming a decoction of the whole plant is inhaled to assuage headache. In India, Cleome viscosa L. is used to promote digestion and urination relieve the bowels of costiveness, expel intestinal worms and to treat inflammation and fever.

Pharmaceutical interest: The counter-irritant property of Cleome viscosa L. is attributed to isothiocyanates (see Cleome gynandra L.). Cytotoxicity: A number of flavonols characterized from Polinasia dodecandra annihilate efficiently the proliferation of brain cancer cells, non-small cell lung

Subclass Dilleniidae

209

OH OH cancer cells, small cell OH lung cancer cells, ovarOCH OCH ian cancer cells, colon HO O O H CO cancer cells, renal cancer cells, melanoma and OH H CO OCH leukemia cell-lines culOH O O OH tured in vitro with GI50 values of the micro or Fig. 121. Cytotoxic flavonoids from Polinasia dodecandra. nanomolar concentration range (Shi Q et al., 1995). Other cytotoxic natural products characterized from the Cleome species are triterpenes of the dammarane-type (Nagaya H et al., 1997). One of these is polacandrin, characterized from Polinasia dodecandra, which inhibits the proliferation of KB (ED50 : 0.6 µg/mL), the P388 (ED50 : 0.9 µg/mL) and RPMI-7951 (ED50 : 0.62 µg/mL) cell-lines (Shi Q et al., 1992). It will be interesting to learn whether more intensive future research on Cleome viscosa L. will disclose any molecules of chemotherapeutic interest. 3

3

3

3

3

Other properties: Note that the antiseptic, antipyretic, analgesic and antidiarrheal properties of Cleome viscosa L. are confirmed experimentally in methanol and aqueous extracts of the plant. An aqueous extract inhibits the growth of Aeromonas hydrophilla and Bacillus cereus cultured in vitro (Perumal Samy R et al., 1999). A methanol extract at doses of 200, 300, and 400 mg/Kg administered per os alleviates yeast-induced fever in rats in a dosedependent manner and as efficiently as paracetamol given at 150 mg/Kg per os (Devi BP et al., 2003). Given orally at doses of 100, 200, 400 mg/Kg this extract protects mice against several types of pain caused experimentally (Devi PB et al., 2003a). It also inhibits castor-oil-induced diarrhea and prostaglandin E2 -induced diarrhea and reduces gastrointestinal motility in the charcoal meal test in rats. (Devi BP et al., 2002). It will be interesting to know what are the principles involved here. Are these isothiocyanates? An extract of Cleome droserifolia reduces intestinal glucose absorption and increases peripheral and hepatic insulin sensitivity in tetracycline-induced diabetic albino rats and is described as “promising therapeutic value” in the treatment of diabetes mellitus (Nicola WG et al., 1996). References Devi BP, et al. (2003) J Ethnopharmacol 87(1): 11–13. Devi BP, et al. (2003a) Fitoterapia 74(3): 262–266. Devi PB, et al. (2002) Phytomed 9(8): 739–748. Nagaya H, et al. (1997) Phytochem 44(6): 1115–1119. Nicola WG, et al. (1996) Bull Chim Pharm 135(9): 507–517. Perumal Samy R, et al. (1999) J Ethnopharmacol 66(2): 235–240. Shi Q, et al. (1995) J Nat Prod 58(4): 475–482.

Warning: Caution must be taken as the toxic effects of this plant are unknown.

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Capparis zeylanica L. [From Greek, kapparis = caper and from Latin, zeylanica = from Ceylon] Synonymy: Capparis horrida L. F. Common names: Nahmanitanget, nahmanithanjet, nwamanithanleyet (Burmese); govindi, kadambha (Sanskrit); indu, tonbai (Tamil).

Physical description: It is a climbing shrub which grows in the geographical zone, spanning India and the Philippines. The branches are terete, and the young parts are rufous hairy. Leaves: 2.5 cm–7.5 cm × 1.8 cm–5 cm. The petiole is 6 mm long. Stipular hooked prickles are present.The blade is elliptic, oblong, obtuse, acute or retuse, and shows a long and stout midrib. The blade is narrow at the base, reticulately veined, glabrous and glossy above. The flowers are supraaxillary, solitary or grouped in twos or threes. The calyx comprises of 5, 9 mm long sepals which are densely rufous pubescent outside and very concave. The petals are twice as long as the sepals and densely rufous. The gynophore is 3.2 cm long. The ovary is ellipsoid and apiculate. The fruits are subglobose and 4 cm long capsules supported by a thick pedicel and containing several seeds (Fig. 122). Pharmaceutical potential: The counter-irritant property of Capparis zeylanica L. is attributed to isothiocyanates (see Cleome gynandra L.). The therapeutic potential of Capparis zeylanica L. remains unexplored.

Uses: In Burma, Capparis zeylanica L. is a counter-irritant remedy. Internally, the bark is used to treat cholera and the root bark is used to promote digestion. In India, the roots of Capparis zeylanica L. are bitter, cooling, hepatoprotector and sedative (Ayurveda). The leaves are pounded and applied to boils, swollen parts and piles. In the Philippines, the leaves are rubbed with salt and applied to the head in order to assuage headache. In Cambodia, Laos, and Vietnam, Capparis zeylanica L. is invigorating, antiscorbutic and is used to treat gastritis.

Fig. 122. Capparis zeylanica L.

Warning: Caution must be taken as the toxic effects of this plant are unknown.

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211

Crateva magna (Lour.) DC. [After kratevas, a Greek root gatherer of antiquity and from Latin, magnus = great] Physical description: It is a small and handsome riverside tree found in India, South China, Burma, and Malaysia. The bark is smooth; the inner bark mottled with yellow and white. The wood is white and hard. Leaves: deciduous with 3 folioles. The folioles are large elliptic, entire, glabrous, slightly bluish beneath, reticulately veined and 8 cm–17 cm × 4 cm–8 cm. The petiolules are 3 mm–6 mm long and the petiole 3.8 cm–7.6 cm long. The lateral folioles are oblique at the base, and the folioles show 10–15 pairs of secondary nerves. The flowers are arranged in long pediceled terminal heads, which are 5 cm large and showy. The flowers comprise of a disc-shaped receptacle, several green white ripening cream sepals, and 13–25 thread-like, pinkish purple and showy stamens. The fruits are globose, 4 cm long capsules supported Synonymy: Crateva nurvulana by a 12 cm long gynophore. The seeds Buch-Ham. are numerous, horseshoe-shaped and embedded in a pulp (Fig. 123). Common names: Kadet (Burma); cadat, dangla (Malay); ajapa (Sanskrit); varanam (Tamil).

Fig. 123. Crateva magna (Lour.) DC. From: KLU 36620. Field collector & botanical identification: Lynwood M. Hume, 10 Oct 1983. Geographical localization: Kg. Panji Alam, Kuala Terengganu, in house yard, apparently cultivated, altitude C. 10 m, East Malaysia.

Uses: In India, the bark of Crateva magna (Lour.) DC. is used to relieve the bowels of costiveness and to expel intestinal worms. The flowers are used to assuage liver congestion. In Indonesia, the bark of Crateva magna DC. is pounded with water and applied to the skin to treat fever and muscular pain. The leaves and other ingredients are used to make an external remedy to cure mental illnesses. In Malaysia, the leaves, the roots and the bark are boiled in oil and the mixture obtained is applied to the body to stop flatulence. The bark is bitter and flavoring, and the juice expressed from it is drunk to stimulate appetite and to relieve the bowels of costiveness. The leaves are counter-irritant.

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Pharmaceutical interest: Lupeol isolated from the stem bark of Crateva magna (Lour.) DC. reduces the foot-pad thickness and complement activity in arthritic rats suggesting that the anti-inflammatory activity of triterpenes may be due to their anticomplementary activity (Geetha T et al., 1999). Lupeol, given at 25 mg/Kg decreases the levels of lactate dehydrogenase, inorganic pyrophosphatase, alkaline phosphatase, γ -glutamyl transferase and βglucuronidase in the urine of rats, experimentally poisoned with oxalic acid (Malini MM et al., 1995).

HO

Lupeol

References Geetha T, et al. (1999) General Pharmacology 32(4): 495–497. Malini MM, et al. (1995) Jpn J Med Sci Biol 48(5–6): 211–220.

Warning: Caution must be taken as the toxic effects of this plant are unknown. Stixis scortechinii (King) Jacobs [After Father Scortechini, botanist in Perak, Malaysia during the end of the 19th century] Synonymy: Roydsia scortechinii King., Roydsia parviflora (non Griff.) King. Uses: In Indonesia, the juice expressed from the roots is used to soothe sore eyes. It will be interesting to learn whether more intensive future research on Stixis scortechinii (King) Jacobs will disclose any molecules of therapeutic interest. This species will probably disappear before being assessed for pharmacology.

Physical description: It is a rare twining shrub which grows to a height of 3 m–4 m tall in the rainforests of Sumatra and Malaysia. The stems are terete, smooth and lenticelled. Leaves:

Fig. 124. Stixis scortechinii (King) Jacobs. From: KLU Herbarium 4322. Field collector: LFH Merton, 14 July 1963, 3000 ft, Fraser’s Hill, on the road from the Gap (Pahang) in a large climber on Castanopsis, Malaysia. Botanical identification: L.L. Forman, Royal Botanical Garden, Kew, 1974.

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213

simple, without stipules and spiral. The petiole is 1 cm–1.4 cm long, terete, smooth, glabrous and curved toward the blade.The blade is oblong lanceolate, orbiculate, acute at the base, shortly acuminate at the apex, and 6.5 cm–9 cm × 4.5 cm–2.8 cm. The blade shows 5–6 pairs of secondary nerves which are arching at the margin. The inflorescences are stout and 15 cm–20 cm long terminal racemes. The fruits are green, hard, ovoid, smooth, 3.2 cm–3.5 cm × 2 cm–2.5 cm and very shortly apiculate at the apex, containing a single seed of about 2.4 cm (Fig. 124). Warning: Caution must be taken as the toxic effects of this plant are unknown.

2. Family BRASSICACEAE G. T. Burnett 1835 nom. conserv., the Mustard family Physical description: The family Brassicaceae (or Cruciferae) consists of about 350 genera and 3000 species of annual and perennial pungent herbs. Brassicaceae are easily detectable by their cross-shaped corolla, hence the name crucifers. The pungency and crucifers are imparted to glucosinolates which release isothiocyanates. The leaves are simple, without stipules, and alternate or opposite. The blade is dissected, soft and dull green. The inflorescences are racemes of yellow or white, bisexual and actinomorphic flowers. The calyx consists of 4 free sepals which are imbricate in 2 opposite pairs. The corolla consists of 4 petals. The andrecium consists of 6 stamens, the 2 outer ones shorter than the 4 inner ones (tetradynamous). The anthers are 2-locular and open lengthwise. The gynecium consists of a pair of carpels united into a sessile and single-celled ovary divided by a wall and including several ovaries attached to 1–2 parietal placentas. The fruits are capsular. Pharmaceutical interest: Belonging to the Brassicaceae family are a very large number of vegetables, such as Brassica oleracea L. (cabbage), Brassica nigra (L.) Koch. (mustard) and Sinapis alba L. (radish). Cheiranthus cheiri L. (wallflower) and Lunaria rediviva L. (honesty) are ornamental plants. Isothiocyanates irritate the skin and the mucosa and impart to Brassicaceae counterirritant properties, hence the empirical use of mustard plasters in Western medicine. More recently, isothiocyanates have attracted a great deal of interest on account of their ability to boost the enzymatic activity of detoxification enzymes, including phase II enzyme, glutathione S-transferase (GST) and quinone reductase (QR), hence providing protection against cancer. One such isothiocyanate is 4-methylsulphinyl butyl isothiocyanate from broccoli which promotes the anticarcinogen marker enzyme quinone reductase in murine hepatoma Hepa cells.Armoracia rusticana (horseradish) and Raphanus raphanistrum (wild radish) can be fatal to livestock and are known to induce bloody vomiting and diarrhea in humans, after being ingested in excessive quantities. About 30 plant species of Brassicaceae are medicinal in the Asia-Pacific.

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Brassica juncea (L.) Cosson [From Latin, Brassica = cabbage and juncea = rush-like] Common names: Indian mustard; moutarde de l’Inde, moutarde rouge (French); pak kai (Malay); mostaza (Filipino); mostarde da India (Portuguese); rajika (Sanskrit); kadugu (Tamil).

Physical description: It is a herb which grows to a height of 40 cm– 50 cm in India, Malaysia, East Asia, Africa, Madagascar, West Indies and South America. The stems are glabrous. Leaves: simple, spiral and without stipules. The petiole is 2 cm–8 cm long, and is longer, channeled and sheathing at the base of the stem. The blade is orbicular, glabrous and 12 cm × 5 cm–4 cm × 1 cm. The apex is obtuse, the margin is laxly toothed and the base is tapered. The blade shows 5–6 pairs of secondary nerves which are flat above and raised below. The inflorescences are terminal and axillary racemes of little yellow flowers. The fruits are capsular, long and thin and contain numerous seeds which are minute (Fig. 125). Pharmaceutical interest: Chemotherapeutic interest: The main constituent of the essential oil of Brassica juncea (L.) Cosson is allyl isothiocyanate. The antiseptic property of Brassica juncea (L.) Cosson is confirmed: the essential oil inhibits the growth of several bacteria and fungi cultured in vitro (Olivier C et al., 1999; Nielsen PV et al., 2000; Shin SW et al.,

Fig. 125. Brassica juncea (L.) Cosson. From: KLU Herbarium 041790. Field Collector: Rohani Bte Hassan, 19 Sep 1990. Botanical identification: Ong HC. Geographical localization: cultivated in garden, Kuala Lumpur, Malaysia.

Uses: The seeds of Brassica juncea (L.) Cosson are pungent and are used in America, Japan, China and other countries to make mustard and oil (canola oil). Canola oil abounds in omega-3 fatty acids and has the potency to lower the risk of stroke. In China, the seeds are used to treat colds, rheumatism, lumbago, abscesses and stomach disorders. The leaves are used to soothe inflammation of the bladder and to stop hemorrhages. In Malaysia, the oil expressed from the seeds is used to treat skin eruptions and to heal ulcers.

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2001) and inhibits proliferation of human prostate cancer cells by causing G2/M arrest and inducing apoptosis (Xiao D et al., 2003). Dietetic properties: In regard to the dietetic property, the N seeds of Brassica juncea (L.) Cosson increase the levC els of bile acids and neutral sterols in the liver and lowS ers the mean number of tumors in the colon and the intestine of rats intoxicated with 1, 2-dimethyl hydrazine Allyl isothiocyanate (Khan BA et al., 1996). The seeds lower the levels of serum cholesterol, low density lipoproteins, very low density lipoproteins, and increase high density lipoproteins in male albino rats fed for 90 days on a standard laboratory rat diet plus 20% coconut (Khan BA et al., 1996a). Note that the essential oil of Brassica juncea (L.) Cosson has been used in cosmetics for hair control (Grdzelidze AM et al., 1968). References Khan BA, et al. (1996) Invest New Drug 14(4): 365–369. Khan BA, et al. (1996a) Plant Foods for Human Nutrition 49(4): 295–299. Grdzelidze AM, et al. (1968) Mezhdunar, Kongr. Efirnym Maslam, [Mater.], 4th. 1: 89–90. Pishchevaya Promyshlennost, Moscow, USSR. CA 79: 83398. Xiao D, et al. (2003) Carcinogenesis 24(5): 891–897.

Capsella bursa-pastoris (L.) Medic. [From Latin, capsella = little box and from bursa = sac and pastorem = shepherd] Common names: Shepherd’s purse, blind-weed, toy-wort, mother’s head; ch’i (Chinese); bourse a` pasteur (French); te thai, dinh lich, co tam giac (Cambodian, Laos, Vietnamese).

Physical description: It is an herb which grows to a height of 60 cm, mostly in temperate regions, in open ground, on walls and drains. The stems are terete, glabrous or hairy. Leaves: small and rosulate. The blade is oblong, acute or oblanceolate, and lobed or inciso-pinnatifid. The flowers are at first corymbose, then elongate into 20 cm–22.5 cm long racemes. The

Uses: Capsella bursa-pastoris is well-known in Europe and North America for its use to check bleeding, treat dropsy and promote urination. In China, the ashes of the roots and leaves are used to treat flux. A powder of the plant is used to soothe inflammation. The plant is used to improve liver health, stop dysentery, treat fever, promote urination and check bleeding. In Cambodia, Laos, and Vietnam, a decoction of the entire herb (6 g/day–12 g/day) is drunk to stop haemoptysis and uterine bleeding, and to treat pulmonary oedema and fever.

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calyx comprises of 4 oblong and obtuse sepals. The corolla is crossshaped, and consists of 2 pairs of white petals which are oblanceolate, and about half as long as the sepals. The fruits are heart-shaped flattened capsules which are notched at the apex, dehiscent, 9 mm × 4 mm–5 mm, and contain several (up to 30 000 per plant), ellipsoid, reddish brown and very small seeds (Fig. 126). Pharmaceutical interest: Acetylcholine: A curious feature of Capsella bursa-pastoris (L.) Medic. is that it contains acetylcholine. Acetylcholine is a neurotransmitter, responsible for the parasympathetic neurotransmission in our organism. One might therefore set the hypothesis that the presence of acetylcholine could explain the diuretic property of the plant, by the activation of muscarinic Fig. 126. Capsella bursa-pastoris (L.) Medic. receptors resulting in the contraction of the ureter and the bladder. Acetylcholine could O H3C + also be responsible for the antifebrile properties of Capsella bursa-pastoris, since it is known to HH3CC N O CH3 3 stimulate the secretion of sweat. An anti-ulcer property is also probable. Acetylcholine Chemotherapeutic interest: A benzenic extract of Capsella bursa-pastoris (L.) Medic. reduces the number of bacteria and yeasts cultured in vitro (El-Abyad MS et al., 1990) on a probable account of luteolin-7-rutinoside and quercetin-3-rutinoside. An extract of the plant given to mice (0.14 g/Kg/d) experimentally infested with Ehrilch solid tumors reduces by 50%–80% the proliferation of tumors. Fumaric acid was characterized as the active principle and was able to annihilate efficiently the tumors at a dose of 10 mg/Kg/day. This compound is moderately toxic with a lethal dose 50% of 266 mg/Kg (Kuroda K et al., 1976). Other pharmacological properties: The plant is known to exert other manifold pharmacological properties. Extracts display diuretic, anti-inflammatory, antiulcer (Kuroda K et al., 1969), cardiovascular (Kuroda K et al., 1969a) and haemostatic properties (Kuroda K et al., 1969b). The haemostatic principle is bursinic acid.

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References El-Abyad MS, et al. (1990) Microbios 62(250): 47–57. Kuroda K, et al. (1969) Arch Int Pharmacodyn Ther 178(2): 392–399. Kuroda K, et al. (1969a) Arch Int Pharmacodyn Ther 178(2): 382–391. Kuroda K, et al. (1969b) Life Sci 8(5): 151–153. Kuroda K, et al. (1976) Cancer Res 36(6): 1900–1903.

Warning: Note that this herb accumulates heavy metals when grown in town. Cardamine hirsuta L. [From Greek, name kardamon ´ = an Indian spice and from Latin, hirsutus = hairy] Common name: Hairy bittercress.

Physical description: It is an invasive herb which grows to a height of 30 cm. It grows in vacant lots of land in several temperate countries. The stems are glabrous and erect from a rosette of leaves. Leaves: numerous, pinnately lobed, 2 cm–5 cm long, spiral and without stipules. The petiole is channeled and sheathing at the base, and subglabrous. The blade is glabrous or subglabrous and shows a few pairs of indistinct secondary nerves. The inflorescences are terminal or axillary, corymbose and 1 cm long racemes. The flowers are white and small. The calyx comprises of 2 pairs of sepals, which are subglabrous, and 2 mm × 0.5 mm long. The corolla consists of 2 Fig. 127. Cardamine hirsuta L. From Herbarpairs of petals which are very thin, and ium 35014. Plants of Maryland. Field collector pure white. The fruits are 1 cm–2 cm × & botanical identification: JD Postman, 17 Mar 1 mm capsules containing numerous 1974. Geographical localization Kensington, 3505 Astoria Road, in full sunlight. seeds which are very small. The fruit pedicel is 4 mm–1 cm long pedicels (Fig. 127). Pharmaceutical interest:The pharmacological potential of Cardamine hirsuta L. remains unexplored. A methanolic extract of Cardamine angulata displays

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antiviral activity against the Herpes Virus type 1 (McCutcheon AR et al., 1995). Cardamine opizii has been used to treat diabetes (Kvetensky J, 1967). It will be interesting to learn whether further studies on Cardamine hirsuta L. will disclose any principles of pharmaceutical value.

Uses: In Laos, Vietnam, and Cambodia, Cardamine hirsuta L. is used to stop dysentery and to treat eye trouble. Note that the leaves are eaten in salads.

References Kvetensky J (1967) Cas Lek Cesk 106(6): 163–165. McCutcheon AR, et al. (1995) J Ethnopharmacol 49(2): 101–110.

Warning: Caution must be taken as the toxic effects of this plant are unknown. Nasturtium indicum DC. [From Latin, nasus tortus = twisted nose and indicum = from India] Pharmaceutical interest: It is an invaSynonymy: Nasturtium sive herb which grows to a height of madagascarience Wight., Sinapis 45 cm in Asia. The stems are sucdivaricata Roxb. culent, glabrous or hairy, and terete. Common names: Indian cress; cai Leaves: simple, 7.5 cm × 2.5 cm and cot xoi, dinh lich, lai hoang, thuy gioi without stipules. The blade is ovatethai (Vietnamese). lanceolate, and runcinate-dentate. The inflorescences are terminal and long racemes of several small and bright yellow flowers. The flower pedicels are 3 mm–6 mm long. The fruits are 1.2 cm– 2 cm long capsules which are straight or slightly curved and contain several seeds. The seeds are very small, 2-seriate and red. Pharmaceutical interest: Nasturtium Uses: In Cambodia, Laos, and indicum DC. contains sinigrin, a gluVietnam, Nasturtium indicum DC. is cosinolate, which is the precursor of used to promote urination, invigorate allylisothiocyanate (Pulverer G et al., health and treat scurvy. The seeds 1969). Sinigrin inhibits the initiaare used to treat asthma. tion and promotion phases of 4-nitroquinoline 1-oxide-induced rat tongue cancer. References Derrick E, et al. (1997) Br J Dermatol 136(2): 290–291. Hecht SS, et al. (1995) Cancer Epidemiol Biomarkers Prev 4(8): 877–884. Pulverer G, et al. (1969) Ger Med Mon 14(1): 27–30.

Warning: A number of plants classified within the genus Nasturtium cause contact dermatitis (Derrick E et al., 1997).

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Nasturtium officinale R. Br. [From nasus tortus = twisted nose and officinale = used in medicine] Synonymy: Nasturtium fontanum Aschers. Common names: Water-cress; cresson aquatique (French); nasturzio (Italian); agriao (Portuguese); berro (Spanish).

Physical description: It is a herb about 50 cm tall which grows mainly in the watery pastures of Europe and the temperate parts of Asia.The stems are succulent and glabrous. Leaves: spiral, without stipules, 4 cm–8 cm long and pinnately lobed. The petiole is sheathing at the base. It is channeled, the channel filled with hairs. The blade shows 4–5 pairs of opposite or sub-opposite lobes of 4 mm– Fig. 128. Nasturtium officinale R. Br. From: KLU Herbarium 35336. Plants of Connecticut. 1 cm in diameter and a terminal lobe Geographical localization: Collier Road, Hartwhich is obscurely 5-lobed. Each lobe ford Co., Wethersfield. Field collector & botanishows 2–3 pairs of nerves, which are cal identification: Steven R Hill, 28 May 1981. flat above and raised below. The inflorescences are terminal or axillary corymbs of very small flowers which comprise 4 sepals and 4 white petals (Fig. 128). Pharmaceutical interest: Antioxidant and anti-inflammatory propUses: In China, Nasturtium officinale erties: One might set the hypothesis R. Br. is used to soothe inflamed that the anti-inflammatory properties of lungs, throat and mouth. In Indonesia, Nasturtium officinale R. Br. are posthe plant is used to treat scurvy. In sibly attributed to a synergistic action Laos, Cambodia and Vietnam, the of flavonoids and isothiocyanates. A plant is used to treat scurvy and to number of flavonoids isolated from promote urination. Nasturtium officinale R. Br. inhibit the release of histamine, a mediator of inflammation, in antigen-stimulated RBL2H3 cells in vitro experiment (Goda Y et al., 1999). In addition, consumption of Nasturtium officinale R. Br. is known to decrease oxidative metabolism. The ingestion of Nasturtium officinale R. Br. reduces the oxidative metabolism of acetaminophen in a cross-over trial on human volunteers (Chen L et al., 1996).

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Antitumor properties: In smokers, phenethyl isothN iocyanate released upon the chewing of NasC S turtium officinale R. Br. protects against lung cancer (Hescht SS et al., 1995). It inhibits the oxidative metabolism of the tobacco-specific lung carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1Phenethyl isothiocyanate butanone and lowers therefore the risks of lung cancer (Hecht SS et al., 1995). Cruz (1970) reported a remarkable antimitotic action of Nasturtium officinale R. Br. on some experimental tumors. References Chen L, et al. (1996) Clin Pharmacol Ther 60(6): 651–660. Cruz A (1970) Hospital (Rio J.) 77(3): 943–952. Derrick E, et al. (1997) Br J Dermatol 136(2): 290–291. Goda Y, et al. (1999) Biol Pharm Bull 22(12): 1319–1326. Hecht SS, et al. (1995) Cancer Epidemiology, Biomarkers & Prevention 4(8): 877–884.

Warning: A number of plants classified within the genus Nasturtium cause contact dermatitis (Derrick E et al., 1997). H. Order ERICALES Lindley 1833 The order Ericales consists of 8 families and about 4000 species of shrubs, treelets and herbs which are thought to have originated from the order Theales somewhere in the family Actinidiaceae (Appendix I). Ericales are mycotrophic, which means that they depend on mycorhizal fungus to survive. Ericaceae is the largest family of Ericales.

1. Family EPACRIDACEAE R. Brown 1810 nom. conserv., the Epacris Family Physical description: The family Epacridaceae consists of 30 genera and 400 species of shrubs which are well-represented in Australia and New Zealand. It is known to produce ursolic acid, methylsalicylate, iridoids, tannins, flavonoids (foeniculin) and proanthocyanins. The leaves of Epacridaceae are simple, hard, and without stipules.The inflorescences are racemes.The flowers are perfect, regular and hypogynous.The perianth comprises of 5 sepals which are free and persistent in fruits, and a 5-lobed tubular corolla. The andrecium includes 5 stamens which alternate with the corolla lobes. The filaments are free and attached to the corolla tube. The anthers are bisporangiate, monothecal and open by longitudinal slits.The gynecium consists of 5 carpels united into a compound, plurilocular ovary with parietal placentas to which are attached several ovules. The fruits are loculicidal capsules or drupes.

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Pharmaceutical interest: Belonging to the family Epacridaceae are several ornamental plants. The pharmacological potential of the family Epacridaceae is yet to be discovered and it will be interesting to learn whether more intensive future research on this family will disclose any molecules of therapeutic interest. Styphelia Malayana (Jack) J.J. Sm. (Leucopogon Malayanus Jack) is used in Malaysia for medicinal purposes. Leucopogon Malayanus Jack [From Greek, leukos = white, pogon = beard, and from Latin, malayanus = From Malaya ] Synonymy: Styphelia malayana (Jack) J.J. Sm. Common names: Maki cina, atap, tasek timbul (Malay). Uses: In Malaysia, Leucopogon malayanus Jack is used to assuage body aches and stomach-ache. The pharmacological potential of Leucopogon Malayanus Jack is yet to be discovered.

Physical description: It is a shrub which grows to a height of 4 m in the mountains of Southeast Asia at 3000– 4000 feet altitude. The stem bark is greyish, ashy, fairly hairy at the apex, deeply fissured and with numerous leaves-scars. Leaves: simple, spiral, sessile and without stipules. The blade is 2.5 cm–3.3 cm × 4 mm–5 mm, velFig. 129. Leucopogon Malayanus Jack. vety below, elliptic-lanceolate, thick, From: KLU Herbarium 17228. Field Collector: acuminate at the apex and without 12 July 1971, SC Chin. Botanical Identificanerves. The inflorescences are very tion: Benjamin C Stone 1972. Geographical small hairy spikes. The flowers com- localization: Pahang, Genting Highlands, near prise 5 mm–1 mm long sepals. The 5 Selangor border. In a dense Ericaceous mountain forest, Malaysia. petals of the corolla are 2 mm × 1 mm. The stigma is hairy at the base and 2 mm long. The fruits are little red and glossy berries (Fig. 129). Warning: Caution must be taken as the toxic effects of this plant are unknown.

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2. Family ERICACEAE A. L. de Jussieu 1789 nom. conserv., the Heath Family Physical description: The family Ericaceae consists of 125 genera and 3500 species of shrubs and treelets known to contain iridoid, phenolic glycosides and tannins. Ericaceae are widespread in temperate and subtropical regions and in tropical mountains. Note that the presence of iridoids in Ericaceae suggests that the family should be classified in the Asteridae rather than Dilleniidae. In this family the leaves are simple, small, firm and without stipules. The flowers are perfect, regular, hypogynous and arranged in bracteate racemes. The calyx and corolla consist of 3–7 sepals and petals. The corolla is tubular and often urceolate, and 5-lobed. The andrecium consists of 2 whorls of 5 stamens attached directly to a nectary disc. The anthers are dorsifixed, tetrasporangiate, dithecal and open by apical pores. The gynecium consists of 2–10 carpels united to form a compound and plurilocular ovary which encloses several ovules attached to axile (below) and parietal (above) placentas. The fruits are dehiscent capsules, berries or drupes. The seeds are small and winged.

HO HO H

H

H O H

OH

OH

O

OH

OH

O

OH H

OH Arbutin

Hydroquinone

Pharmaceutical interest: Belonging to the family Ericaceae are numerous outdoor shrubs and rock-garden plants such as Rhododendron and Erica. Other examples of useful Ericaceae are Erica arborea L. (briar root wood) and Ledum groenlandicum Oeder (Labrador tea). A number of Ericaceae, including Arctostaphylos uva-ursi (L.) Spreng. (Bearberry, French Pharmacopeia, 10th Edition), Arbutus unedo L. (arbousier), Chimaphila umbellata Nutt. (herbe a pisser), Calluna vulgaris (L.) Hull. (Scotch heather) L. and Erica cinerea L. (twisted heath) are used in Western medicine to promote urination and to treat urinary tract infections. This property is attributed to phenol glycosides such as arbutin, the precursor of hydroquinone. Note that hydroquinone inhibits the synthesis of melanin and has been used more or less successfully to bleach the skin. Gaultheria procumbens L. (tea berry) is the source of wintergreen oil which is rich in methyl salicylate. The berries of Vaccinium myrtillus or blueberry, bilberry (Myrtillus, Swiss Pharmacopoeia, 1934) are used to extract anthocyanins. Note that several Ericaceae, especially the

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Rhododendron species, are neurotoxic on account of unusual tetracyclic diterpenes known as grayanatoxins. Of recent interest are flavonoids from Rhododendron dauricum which demonstrated potent anti-HIV activity in vitro. About 20 species of plants classified within the family Ericaceae are used for medicinal purposes in the Asia-Pacific. These are often used to treat rheumatism and skin infection, and to stop itchiness. Lyonia ovalifolia (Wall.) Drude [After J. Lyons, a Scottish-American horticulturist of the 19th century; and from Latin, ovalis = ovoid and folium = leaf] Common names: Staggerbush; aynar (Himalayan); nejiki (Japanese).

Physical description: It is a tree which grows in the mountains of India, China and Japan. It is very common in the Himalayas. The stems are smooth, greyish and rusty tomentose at the apex. Leaves: simple, alternate and without stipules. The petiole is 2 mm–6 mm long and rusty tomentose. The blade is papery, tomentose beneath, and 3.8 cm × 2.6 cm × 9 cm×5.5 cm. The base of the blade is cordate and somewhat asymmetrical, the apex is acuminate, and the margin is obscurely wavy and recurved. The blade shows a midrib which is Fig. 130. Lyonia ovalifolia (Wall.) Drude. From: Flora of Malaya, 08010. Field collecflat above and raised below, and 12– tor: 4 May 1964, MED Poore. Geographical 16 pairs of secondary nerves which localization: altitude 6600 ft, Gunong Brinchang are arching toward the apex. The ter- forest ridge, Cameron Highlands, Pahang, tiary nerves are scalariform and visible Malaysia. Botanical identification: FSP Ng. beneath. The inflorescences are terminal spikes of about 5 cm long (Fig. 130). Pharmaceutical interest: The toxic Uses: In China, the leaves and fruits property of Lyonia ovalifolia (Wall.) of Lyonia ovalifolia (Wall.) Drude are Drude is most probably attributed to used to invigorate but are known to a series of diterpenes lyoniatoxins be toxic. (lyoniols), which are known to occur in Lyonia ovalifolia Drude var. elliptica Hand.-Mazz. (Fukuma H et al., 1969; Hikino H et al., 1970; Yasue M et al., 1970; 1971; 1974). The pharmacotoxicological properties of Lyonia ovalifolia (Wall.) Drude remains unexplored til to date.

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References Fukuma H, et al. (1969) Yakugaku Zasshi 89(3): 382–388. Hikino H, et al. (1970) Chem Pharm Bull 18(4): 852–854. Yasue M, et al. (1970) Yakugaku Zasshi 90(7): 893–898. Yasue M, et al. (1971) Yakugaku Zasshi 91(3): 358–362. Yasue M, et al. (1974) Yakugaku Zasshi 94(10): 1349–1352.

Warning: This plant is toxic. Rhododendron moulmainense Hook [From Greek, rhodon = rose and dendron = tree and moulmainense = Moulmain] Synonymy: Rhododendron westlandii Common name: Moulmainense. Westland’s rhododendron

Physical description: It is a magnificent shrub which grows to a height of 2 m. It is found on open hillsides

Fig. 131. Rhododendron moulmainense Hook. From: KLU Herbarium 375. Flora of Malaya. Field Collector: Benjamin C Stone 15 May 1969. Geographical localization: Gunong Jerai, (Kedah Peak) 2800 ft. Botanical Identification: FSP Ng, 11/74.

Uses: In Tibet, the honeys of Rhododendron moulmainse Hook. are used for food and responsible for poisoning. The poisonous principles involved are a series of grayanotoxins (andromedotoxins) which occur in all parts of the Rhododendron species, including pollen. These diterpenes bind to the sodium channels in neurone membranes, increase the permeability of neurones to sodium ions, and hamper normal neurotransmission, hence resulting in a lowering of blood pressure, lack of coordination, convulsions, severe vertigo, hallucinations, bradycardia, feeling of retrosternal compression progressive paralysis and death by paralysis of the diaphragm (Von Malottki K et al., 1996). Grayanatoxins are interesting because they inhibit the mitotic activity of lymphocytes at doses of 10−4 M and 10−3 M (Ascioglu M et al., 1998). Other secondary metabolites of interest in the Rhododendron species are flavonoids, such as quercetin from Rhododendron cinnabarium which inhibits experimentally-induced production of tumor necrosis α and nitric oxide by macrophages (Manjeet KR et al., 1999).

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in forests and thickets from 1300 to 12 000 ft. in R 1 R2 H H South China, (Southeast Tibet to Guangdong), Taiwan, Laos, Vietnam, Cambodia and Malaysia. The bark is grey, fissured longitudinally and glabrous. Leaves: simple, without stipules, sessile and spiHO OR3 OH ral, and the young leaves reddish. The blade is HO elliptic, olive, glossy, lanceolate, glabrous, leathery Grayanotoxin and 10.4 cm–5.6 cm × 1.6 cm–3 cm. The margin is recurved, and the blade shows a few pairs of indistinct secondary nerves. The midrib is sunken above and raised below. The inflorescences are terminal and bracteate spikes of about 5 cm–6 cm long. The bracts are broad, 7 mm × 8 mm, acute and hairy at the margin. The flowers are mildly fragrant and showy. The corolla is pure white, or white flushed with yellow or pink, magenta or lilac, and is with or without a yellow or pale green blotch. The corolla is tubular and 5-lobed. The corolla tube is 8 mm × 3 mm and the lobes are elliptic, irregular, very thin and nerved. The andrecium consists of 10 stamens with 2 mm×0.5 mm anthers. The filaments are 1.8 cm– 2.3 cm long and pilose at the base. The ovary is fusiform, glabrous and 4 mm long. The style is 3 cm long. The fruits are capsules marked at the apex by vestigial styles (Fig. 131). References Ascioglu M, et al. (1998) J Int Med Res 21(7): 140–143. Manjeet KR, et al. (1999) Int J Immunopharmacol 21(7): 435–443. Von Malottki K, et al. (1996) Deutsche Medizinische Wochenschrift 121(30): 936–938.

Warning: The plant is toxic. Vaccinium vitis-idaea L. [From Latin, vaccinium = whortleberry and vitis-idaea = vine of Mount Ida] Common names: Lingonberry, cowberry, red whortleberry.

Uses: In China and Japan, Vaccinium vitis-idaea L. is used to treat gonorrhea. The dried leaves (Cowberry leaf, Japanese Pharmacopoeia, 1961) are astringent and have been used as a domestic Japanese remedy for the treatment of diarrhea and rheumatic conditions. The plant contains arbutin, the forerunner of hydroquinone which is well known for its urinary antiseptic properties.

Physical description: It is a 7 cm– 10 cm tall, woody and creeping herb found in China, Japan and Australia. The stems are microscopically hairy. Leaves: simple, spiral and without stipules. The petiole is 0.5 mm long. The blade is coffeebean-like, broadly elliptic, notched at the apex, 7 mm × 4 mm–4 mm × 2 mm, and glabrous except for a few hairs

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underneath. The midrib is sunken above. The margin is laxly serrate. The fruits are berries of 7 mm in diameter (Fig. 132). Pharmaceutical interest: Tannins: In regard to the antidiarrheal and anti-inflammatory properties mentioned above, one might set the hypothesis that condensed tannins such as cinnamtannin B1, proanthocyanidins A1 and epicatechin-(4β → 6)-epicatechin-(4β → 8, 2β → O → 7)-catechin which display strong antioxidant properties experimentally Fig. 132. Vaccinium vitis-idaea L. (Ho KY et al., 1999) are involved. Epicatechin-(4 β → 8)-epicatechin-(4β → 8, 2β → O → 7)-catechin inhibits the proliferation of the periodontal pathogen Porphyromonas gingivalis and Porphyromonas intermedia cultured in vitro (Ho KH et al., 2001). Such tannins are notably present in tea. A water extract of Vaccinium vitis-idaea L. inhibits platelet activating factor-induced exocytose in vitro, thereby confirming the anti-inflammatory property (Tunon H et al., 1995). OH OH OH OH

HO

O

OH OH

HO

OH

O

O

O

OH OH

Epicatechin - (4β → 6) - epicatechin - (4β → 8, 2 β → O → 7) - catechin

References Ho KY, et al. (1999) J Pharm Pharmacol 51(9): 1075–1078. Ho KY, et al. (2001) J Pharm Pharmacol 53(2): 187–191. Tunon H, et al. (1995) J Ethnopharmacol 48(2): 61–76.

Warning: Caution must be taken as the toxic effects of this plant are unknown.

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I. Order EBENALES Engler 1892 The order Ebenales consists of 5 families and about 1700 species of primitive trees and shrubs which are thought to have originated from the order Theales, alongside the Primulales (Appendix I). About a quarter of the species in Ebenales belong to the family Ebenaceae.

1. Family EBENACEAE Gurke in Engler & Prantl 1891 nom. conserv., the Ebony Family Physical description: The family Ebenaceae consists of 5 genera and about 450 species of tropical timbers and shrubs. The wood of Ebenaceae is very dense, hard and reddish. The wood contains notably 1,4 naphthoquinones (plumbagin and 7 – methyljuglone) that darken upon light exposure. Other notorious secondary metabolites of Ebenaceae are a series of pentacyclic triterpenes of the ursane and oleanane type, and some lignans. The leaves of Ebenaceae are simple, leathery, alternate and without stipules. The flowers are small, regular, hypogynous, and principally unisexual (dioecious). The calyx is 3–7-lobed, persistent, and often vestigial in fruits. The corolla is sympetalous, 3–7-lobed. The stamens are attached to the base of the corolla tube, and are usually twice as many as the corolla lobes. The gynecium consists of 2–10 carpels, forming a compound, plurilocular ovary containing several ovules attached to axile placentas. The fruits are very characteristic juicy or leathery berries marked at the base with a vestigial calyx. O H3C

OH

O

7 Methyljuglone

H

H

H

H H

H H Ursane

H Oleanane

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Pharmaceutical interest: Classical examples of Ebenaceae are Diospyros ebenum Konig. (ebony), Diospyros virginianum L. (persimmon) and Diospyros kaki L. f. (Japanese persimmon). Ebenaceae are interesting because they contain a series of antibacterial, antiviral, cytotoxic, monoamine oxidase-inhibitors and antioxidant monomer, dimmers and oligomers of naphthoquinones, and it would not be surprising should more intensive future research on this family disclose any molecules of therapeutic interest. About 20 species of Ebenaceae are used for medicinal purposes in the Asia-Pacific. Note that medicinal Ebenaceae are often used to expel intestinal worms and to treat viral infections. Diospyros argentea Griff. [From Greek, diospyros = persimmon fruit and from Latin, argentum = silver] Common name: Silver-leaved ebony; bedil lalat (Malay).

Physical description: It is a lowland timber of Malaysia and Indonesia. The whole tree is covered in a golden irritating silky tomentum, except the upper side of the leaves and the bark. Leaves: simple, oblong, leathery, and 7 cm × 30 cm. The petiole is stout and up to 1.5 cm long. The base is round and the apex pointed. The midrib is Fig. 133. Diospyros argentea Griff. deeply sunken above and conspicuously raised below. The secondary nerves are indistinct on both sides of the blade.The flowers are white.The fruits are 6 cm×3 cm, velvety, golden-colored, and show 4 sepals at the base which are leathery (Fig. 133). Pharmaceutical interest: To date, the pharmacological potential of Diospyros argentea Griff. is unexplored, but several naphthoquinones and pentacyclic triterpenes have thus far been characterized from the genus Diospyros

Uses: Malays burn the leaves of Diospyros argentea Griff. to repel mosquitoes and apply the pounded roots externally to treat herpes zoster.

(Mallavadhani UV et al., 1998).

Naphthoquinones: Cytotoxic, antibacterial and inhibit the enzymatic activity of monoamine oxidase. The cytotoxicity of naphthoquinones implies at least 3 synergistic mechanisms. Firstly, the quinone moiety has a chemical structure similar to ubiquinone, and interferes with the mitochondrial electron transport.

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Secondly, the quinone moiety generates highly reactive free radicals (Lown JW, 1979). Thirdly, naphthoquinones are planar, and intercalate with DNA. An example of a naphthoquinone of therapeutic interest is atovaquone, which is used to treat malaria and Pneumocystis carinii infection. Examples of cytotoxic naphthoquinones are plumbagin, isodiospyrin and 8 -hydroxyisodiospyrin which inhibit significantly the proliferation of Hepa, KB, Colo-205 and HeLa cell-lines cultured in vitro (Kuo YH et al., 1997). OH H3C O

O

O

OH

CH3 O CH3 OH

O

O Plumbagin

Isodiospyrin

Lemulinol A, a naphthoquinone characterized from the Diospyros species, inhibits mouse liver monoamine oxidase (MAO) activity. An aqueous extract of Diospyros bateri inhibits the proliferation of several sorts of Gram-positive and Gram-negative bacteria cultured in vitro (Odelola HA et al., 1988). Pentacyclic triterpenes: Betulin, betulinic acid and ursolic acid characterized from Diospyros leukomelas, inhibit inflammation (Recio MC et al., 1999). Note that betulinic acid has interesting antiviral properties.

H

R2

R2 H

H R1 H

R1

H

Lupeol R1 = β OH, R2 = CH3

α Amyrin R1 = b OH, R2 = CH3

Betulin R1 = β OH, R2 = CH2OH Betulinic acid R1 = β OH, R2 = COOH

Ursolic acid R1 = b OH, R2 = COOH

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References Cummings CA, et al. (1997) J Vet Diagn Invest 9(3): 311–313. Kapadia GJ, et al. (1997) J Natl Cancer Inst 60(3): 683–686. Kuo YH, et al. (1997) Planta Med 63(4): 363–365. Lown JW (1979) Mitomycin C: Current Status and New Developments. New York: Academic Press. Mallavadhani UV, et al. (1998) Phytochem 49(4): 901–951. Odelola HA, et al. (1988) Afr J Med Scie 17(3): 167–170. Recio MC, et al. (1999) Planta Med 61(1): 9–12.

Warning: 1,4 Naphthoquinones have an irritating odor, cause sneezing, purple color staining to the skin, and are vesicant. 50% of the rats that received weekly subcutaneous injections of a total aqueous extract of Diospyros virginianum L., developed tumors (Kapadia GJ et al., 1978). Animals fed with Diospyros virginiana, were observed to develop gastric impaction, ulceration and perforation. (Cummings CA et al., 1997). Diospyros kaki L. f. [From Greek, diospyros = persimmon fruit and from Japanese, kaki = Diospyros kaki L. f.] Synonymy: Diospyros chinensis Bl. Common names: Japanese persimmon, shi (Chinese).

Physical description: It is a fruit tree native to China, North India, and Japan. The wood is reddish. The stems are smooth, lenticelled, and hairy at the apex. Leaves: simple, alternate and without stipules. The petiole is 1.3 cm–1.5 cm long and hairy. The blade is 8 cm–10.5 cm × 6.4 cm– 7.2 cm, membranaceous, hairy, ovate to broadly elliptic, dark green on the Fig. 134. Diospyros kaki L. f. From: KLU surface and lighter green underneath. Herbarium 22485. Flora Japonica. Ex. Herbario Universitatis Kyotoensis. 1926. Kyoto. Field colThe base of the blade is asymmetri- lector & botanical identification: Q Kadzumi. cal, and the margin is obscurely wavy. From: KLU Herbarium 33036, South China The midrib and secondary nerves are Institute of Botany, Academia Sinica. Kwangflat above and raised below. The flow- chou, China. Field collector & botanical identifiers are axillary and solitary on 5 mm cation: HG Yip, 7 Apr 1981. Geographical localization: Guangzhou, Guangiong, China. pedicels which are hairy. The fruits are yellow berries, which are leathery, glossy and approximately 7 cm in diameter (Fig. 134).

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Pharmaceutical interest: Hypotensive property: The hypotensive property of Diospyros kaki L. f. is attributed to astralagin, kaempferol-3O-(2 -O- galloyl)-glucoside, sisoquercitrin, quercetin-3-O-(2 -O-galloyl)-glucoside which inhibit the angiotensinconverting enzyme dose-dependently (Kameda K et al., 1987).

Uses: In China, the juice expressed from the unripe fruits is drunk to lower blood pressure, check hemorrhage, relieve the bowels of costiveness and treat typhus. The bark and wood are used to heal wounds and ulcers. A decoction of the leaves is drunk to treat fever.

Cellular activities: Japanese persimmon extract, epicatechingallate, and epigallocatechin gallate inhibit the growth of human lymphoid leukaemia Molt 4 cells and calf thymus DNA α-polymerase (Achiwa Y et al., 1997; Umekawa H et al., 1999). Flavonoid glycosides and pentacyclic triterpenes isolated from the leaves protect human neutrophils against experimentally induced neutrophil generation and tyrosyl phosphorylation of proteins (Guang C et al., 2002, Guang C et al., 2002a). A water-soluble acidic arabinogalactan isolated from the leaves of Diospyros kaki L. f. stimulates LPS-induced B lymphocyte proliferation in vitro (Duan J et al., 2003). References Achiwa Y, et al. (1997) Bioscience, Biotechnology & Biochemistry 61(7): 1009–1020. Duan J, et al. (2003) Carbohydrate Research 338(12): 1291–1297. Guang C, et al. (2002) Clinica Chimica Acta 326(1–2): 169–175. Guang C, et al. (2002a) Clinica Chimica Acta 320(1–2): 11–16. Kameda K, et al. (1987) J Nat Prod 50(4): 680–683. Umekawa H, et al. (1999) Biochemistry & Molecular Biology International 47(5): 795–801.

Warning: Caution must be taken as the toxic effects of this plant are unknown. Diospyros wallichii K. & G. ex Williams [From Greek, diospyros = persimmon fruit and after Dr Nathaniel Wallich (1786–1854), a Danish plant hunter, botanist and physician] Physical description: Diospyros walCommon name: Pokok tuba buah. lichii K. & G. ex Williams is a timber which grows to a height of 15 m in lowlands up to 700 m, throughout Malaysia, Burma, Thailand, Sumatra and Borneo. The stems are glabrous, lenticelled and terete. Leaves: simple, alternate and without stipules. The petiole is stout, channeled above, glabrous and 1 cm–1.3 cm long. The blade is elliptic, lanceolate, 21 cm × 7.8 cm–25.9 cm × 8.2 cm, papery and glabrous. The base and the apex of the blade are acute, the margin is somewhat wavy and recurved. The midrib is deeply sunken above and raised below, and the blade shows

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14–18 pairs of secondary nerves which are raised below, while arching and indistinct above. The tertiary nerves are scalariform. The inflorescences are axillary cymes of minute and velvety flowers. The fruits are brown, velvety, globose, and 2.5 cm– 3 cm in diameter. The calyx is vestigial and woody (Fig. 135). The juice expressed from the fruit stains yellow and is very irritating to the skin. Uses: In Malaysia, the leaves of Diospyros wallichii K. & G. ex Williams are used to treat yaws. The fruits are used to poison fish.

Pharmaceutical interest: To date, nothing is known about the therapeutic potential of Diospyros wallichii K. & G. ex Williams. The ichthyotoxicity of the fruits is probably attributed to saponins. The plant may have disappeared before being investigated for pharmacology.

Fig. 135. Diospyros wallichii K. & G. ex Williams. From: KLU 32792. The New York Botanical Garden. Economic Plants of Thailand. Field collectors and botanical identification:Tetsuo Koyama, PJ O’ Connor. 4 Feb 1979. Geographical localization: Peninsular Thailand, Prov. Pangna, Kraburi District, Songphinong waterfall, 50 m alt., tropical forest.

Warning: Caution must be taken as the toxic effects of this plant are unknown.

2. Family STYRACACEAE Dumortier 1829 nom. conserv., the Storax Family Physical description: The family Styracaceae consists of 10 genera and 150 species of tropical timber. The leaves of Styracaceae are simple, alternate, and without stipules. The flowers are perfect, regular, and hypogynous. The calyx is tubular and of 4–5-lobed. The corolla consists of 2–5 petals forming a tube. The andrecium comprises of 4–10 stamens in a single row, and the anthers are linear, tetrasporangiate, dithecal and open by longitudinal slits. The gynecium consists of 3–5 carpels united to form a compound, superior, and unilocular ovary containing several ovules attached to axile placentas. The fruits are capsular are marked by an opening.

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233

Pharmaceutical interest: StyraOR1 caceae is the family of the Styrax species from which balsamic resins RO OR2 are obtained by an incision of the o stems. The resins of Styrax tonkiOCH3 nense Pierre (Siam Benzoin, British Pharmaceutical Codex, 1959), StyNor-lignan rax benzoin Dryand. and Styrax paralleloneurus (Sumatra Benzoin, British Pharmacopoeia, 1948). have been used to make inhalations for the treatment of catarrh whereas Styrax officinalis L., is the source of storax. Of recent interest are antibacterial and antifungal lignans characterized from the Brazilian Styrax ferrugineus. In the Asia-Pacific, Alniphyllum fortunei (Hemsl.) Perk., Alniphyllum hainanense Hay., Styrax benzoin Dryand., Styrax tonkinense Pierre, Styrax benzoides Craib are medicinal. Styrax benzoin Dryand. [From Greek, styrax = Styrax officinalis and from Arabic, luban jawi = frankinscence of Java] Common name: Styrax tree, benzoin tree; kemenyan (Malay).

Physical description: It is a buttressed timber which grows to a height of 30 m in lowland rainforests up to 800 m in Malaysia and Indonesia. The bark is smooth, or finely cracked. The inner bark is soft and reddish and Uses: Benzoin or the resin obtained by bruising then tapping the bark of Styrax benzoin Dryand. has long been used in Asian medicine. It is used to treat stroke, invigorate health after labor, assuage pain in the heart and abdomen, counteract putrefaction, promote libido and heal hemorrhoids. Benzoin contains a large amount of free benzoic acid and cinnamic acid.

Fig. 136. Styrax benzoin Dryand. From: KLU Herbarium 26425. Flora of Selangor. Comm. Ex. Herb. Hort. Bot. Sing. Geographical localization 4 34 m.s., Genting Highlands, Ulu Gombak, altitude: 3000 ft., 14 Jun 1973, Malaysia. Field collectors: Mohd Shah and Mohd Ali.

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the sapwood is white. Leaves: simple, alternate and without stipules and 6 cm– 20 cm × 2.5 cm–9 cm. The blade is glaucous and covered with a glaucous tomentum of starry hairs. The inflorescences are racemose or paniculate. The fruits are globose, glaucous and 2 cm–3.8 cm (Fig. 136). Pharmaceutical interest: A number of lignans characterized from Styrax ferrugineus show antibacterial and antifungal properties (Pauletti PM et al., 2000). These lignans are likely to be cytotoxic and antiviral, but this has yet to be confirmed. The fruits of Styrax japonica contain anti-sweet triterpenes saponins (Yoshikawa K et al., 2000). References Pauletti PM, et al. (2000) Phytochem 55(6): 597–601. Yoshikawa K, et al. (2000) Chem Pharm Bull (Tokyo) 48(7): 1093–1096.

Warning: Caution must be taken as the toxic effects of this plant are unknown.

J. Order PRIMULALES Lindley 1833 The order Primulales consists of 3 families and about 1900 species of shrubs and herbs close to Ericales and Ebenales, with which it shares the ability to use benzoquinones, triterpenoid saponins and flavonoids as chemical repellents (Appendix I). The largest family of this order is the Myrsinaceae with a thousand species. Besides the Myrsinaceae is the family Primulaceae, the family of Primula veris (cowslip, primrose), the flowers and the roots of which have been used to treat insomnia, stress, cough, and skin diseases in Western medicine. The therapeutic potential of Primulales is yet to be fully investigated.

1. Family MYRSINACEAE R. Brown 1810 nom. conserv., the Myrsine family Physical description: The family Myrsinaceae consists of 30 genera and approximately 1000 species of tropical trees, shrubs and herbs abounding with 1, 4-benzoquinones and saponins. The bark is smooth or lenticelled. The leaves in Myrsinaceae are simple, alternate, crenate, fleshy, glossy, and characteristically gland-dotted beneath the blade. The flowers are small, perfect, hypogynous or half epigynous sympetalous, and 5-merous. The calyx consists of 4–5 sepals which are free or connate at the base. The corolla is tubular or rotate. The andrecium consists of 5 stamens adnate to the corolla tube and opposite the petals. The gynecium consists of 3–5 carpels forming a compound single-celled and superior ovary developing upwards into a short style, and containing a few or numerous ovules attached to a free central placenta. The fruits are berries or drupes.

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235

Pharmaceutical interest: Classical examples of Myrsinaceae are Ardisia crenata Sims (Christmas berry) and Ardisia japonica Bl. (Japanese Ardisia) which are ornamental. Myrsinaceae are interesting because they produce quinones and saponins which have so far displayed a large spectrum of pharmacological activities. Of particular interest are saponins characterized from Myrsine africana which could be of chemotherapeutic value. About 40 species of the plants classified within the family Myrsinaceae are used for medicinal purposes in the Asia-Pacific. Note that these plants are often used to treat uterine disorders and sore throat, and to assuage pains. Ardisia crispa A. DC. [From Greek, ardis = sharp and from Latin, crispus = curled] Physical description: It is a shrub Synonymy: Ardisia hortorum Maxim., which grows to a height of 3 m. It Ardisia crispa var. angusta Clarke, is found in the wilds or cultivated Ardisia crenata Sims. in vacant plots, open grounds, vilCommon names: Village ardisia; lages, seashores and the secondary hens eye; mata ayam (Malay). rainforests of Southern Asia. Leaves: 10 cm × 4 cm, simple, alternate and without stipules. The petiole is slender. The blade is narrowly elliptic, tapered toward the apex and the base is dark green, glossy, and succulent. The margin is laxly crenate. The inflorescences are terminal. The flowers are small and whitish-pink. The calyx consists of 5 free sepals. The corolla is short and tubular, and consists of 5 spreading petals. The andrecium comprises of 5 short pediceled stamens with large anthers, with the entire structure forming a conspicuous cone around the style. The fruits are red, glossy, globose and 5 mm long berries (Fig. 137). Pharmaceutical interest: Anti-metastatic properties: Ardisia crispa A. DC produces 2-methoxy-6-tridecyl-1,4-benzoquinone which blocks Uses: The roots of Ardisia crispa A. DC. are used in China to treat fever and to stop excessive salivation. In Malaysia, the juice expressed from the leaves is used to treat scurvy, and an infusion of the roots is drunk to treat fever and cough, and to stop dysentery. In Taiwan, Ardisia crispa A. DC. is used to promote urination.

Fig. 137. Ardisia crispa A. DC.

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platelet aggregation, B16-F10 melanoma cell adhesion to extracellular matrix and B16-F10 melanoma cell invasion, and inhibits pulmonary metastasis and tumor growth by blocking integrin receptor (Fig. 138) (Kang HY et al., 2001) Integrin receptors are transmembrane protein receptors which monitor platelet adhesion within the vasculature during clotting, apoptosis, proliferation, migration, spreading, and adhesion of tumor cells. Ardisiaquinones: An interesting feature of the Ardisia species and Myrsinaceae in general is the production of a very unusual series Fig. 138. Integrin 2-Methoxy-6-tridecyl-1, of dimeric benzoquinones known as 4-benzoquinone blocks integrin receptors and ardisiaquinones. Ardisiaquinone D, E hampers therefore platelet adhesion (PA), and F characterized from Ardisia apoptosis, proliferation, migration, spreading, and adhesion of tumor cells (M). OMS: outer sieboldii inhibit the enzymatic activity membrane surface, CMS cytoplasmic mem5-lipo-oxygenase, a key enzyme of brane surface. pyrogenesis, hence the antifebrile properties mentioned above (Fukuyama Y et al., 1995; Fukuyama Y et al., 1993) Ardisiaquinones G, H and I from Ardisia teysmannia inhibit in vitro the first step of bacterial peptidoglycan synthesis with IC50 of 5 µM, 26 µM and 16 µM respectively (Yang KL et al., 2001). It will be interesting to learn whether more intensive future research on ardisiaquinones will disclose any molecules of therapeutic interest. O OCH3

O

2 - Methoxy - 6 - tridecy - 1,4 benzoquinone

Saponins: Note that Ardisia crispa A. DC. is known to contain ardisiacrispin A and B which contract isolated portions of uterus (Jansakul C et al., 1987). O

O

O OAc

HO

H3CO

Ardisiaquinone G (n= 11)

7 OH

OAc HO O

OH

C

n

O

O

7 HO

R OH

Ardisiaquinone E (R= H)

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References Fukuyama Y, et al. (1993) Chem Pharm Bull 419(3): 561–565. Fukuyama Y, et al. (1995) Chem Pharm Bull 43(8): 1391–1394. Kang YH, et al. (2001) Int J Cancer 93(5): 736–740. Jasankul C, et al. (1987) Planta Med 53(5): 400–409. Piacente S, et al. (1996) J Nat Prod 59(6): 565–569. Yang KL, et al. (2001) Phytochem 58(8): 1235–1238.

Warning: Caution must be taken as the toxic effects of this plant are unknown. Embelia ribes Burm. f. [From Singhalese, aembilla = Embelia ribes and from Arabic, ribas = sorrel] Common names: Common embelia; akar sulur kerang (Malay); amogha (Sanskrit). Uses: The seeds of Embelia ribes Burm. f. are eaten to expel intestinal worms in several Asian countries. In Cambodia, Laos, and Vietnam, the seeds are used to expel intestinal worms. The dried leaves are used to heal pimples and boils. In India, the seeds are used to relieve the bowels of costiveness and to expel intestinal worms. Embelia (British pharmaceutical Codex, 1934), or the dried fruits which must contain about 2.5% of embelin, was used to expel intestinal worms (dose: 4 g–16 g; 60–240 grains) in Western medicine.

Physical description: It is a slenFig. 139. Embelia ribes Burm.f. From: KLU der woody climber which grows in the Herbarium 35271. Flora of Malaya. Geogeographical zone spanning India to graphical localization: Rimbah Ilmu, UniverSouth China. Leaves: simple, alter- sity of Malaya. Woody climber. Field collector: nate and without stipules. The petiole Mustapha. Botanical Identification: BC Stone. is short. The blade is narrowly oval, 13 Apr 1978. 5 cm–10 cm×1.5 cm–5 cm, and shows a few pairs of indistinct secondary nerves. The base of the blade is tapered and the apex pointed. The inflorescences are terminal racemes. The flowers are white or greenish, without a corolla tube. The fruits are black, succulent, tipped and 4 mm long berries (Fig. 139).

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Division MAGNOLIOPHYTA O OH

HO O Embelin

Pharmaceutical interest: Embelin: Embelin is interesting because it is anthelmintic, antibacterial, analgesic, antitumor, anti-inflammatory (Chitra M et al., 1994) and binds to opioid µ- and κ-opioid receptors (Zutshi U et al., 1989). Rats infected with 10 adult Hymenolepsis diminuta tapeworms recover with a diammonium salt of embelin given at 100 mg/kg (Bogh HO et al., 1996). The precise mechanism of action of embelin remains an unanswered and interesting question. In an attempt to answer it, one might set the hypothesis that embelin acts on κ-receptors and therefore modifies the transfer of calcium ions through the cell membrane of helminthes. Praquizantel is an example of a molecule which controls schistosomiasis and Taenia sp. infection through a mechanism involving the transfer of calcium ions. Embelia ribes Burm. f. is most probably antibacterial on account of embelin which exhibits significant inhibition against five and moderate activity against three strains of 12 bacteria cultured in vitro (Chitra M et al., 2003). Potassium embelate subjected to subacute, chronic and reproductive toxicity tests in rodents and monkeys did not cause severe adverse properties (Johri RK et al., 1990). References Bogh HO, et al. (1996) J Ethnopharmacol 50(1): 35–42. Chitra M, et al. (1994) Chemotherapy 40(2): 109–113. Chitra M, et al. (2003) Fitoter 74(4): 401–403. Krishnaswamy M, et al. (1980) Indian J Exp Biol 18(11): 1359–1360. Gupta S, et al. (1989) Contraception 39(3): 307–320. Johri RK, et al. (1990) Indian J Exp Biol 28(3): 213–217. Low G, et al. (1985) Toxicol Appl Pharmacol 81(2): 220–230. Zutshi U, et al. (1989) Indian J Exp Biol 27(7): 656–657.

Warning: A host of evidence suggests that embelin reduces fertility (Krishnaswamy M et al., 1980; Gupta S et al., 1989) and vision (Low G et al., 1985).

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Labisia pumila (BI.) Benth. & Hook. [From Greek, labis = holder and from Latin, pumilus = darwf] Physical description: It is an understorey herb found in the lowlands and hilly rainforests of the Asia-Pacific, which grows to a height of about 30 cm. Leaves: simple, spiral and exstipulate. The petiole is short and thick. The blade is lanceolate, fleshy, light green on the surface and purplish underneath, and slightly toothed. The inflorescences are 12 cm–20 cm long racemes of small and white campanulate flowers.The fruits are black berries (Fig. 140).

Synonymy: Ardisia pumila Bl., Angiopetalum punctatum Reinw., Ardisia pumila var. alata Scheff., Labisia pothoina Lindl., Labisia pumila (Bl.) F-Vill. & Naves, Labisia pumila var. alata (Scheff.) Mez, Labisia punctata (Reinw.) Airy-Shaw. Common names: Common Labisia; selusoh Fatimah, kacip Fatimah (Malay).

Uses: In Malaysia, the roots of Labisia pumila (BI.) Benth. & Hook. are boiled to make a drink ingested to induce labor, stop flatulence and dysentery, regulate menstruation, treat venereal diseases and invigorate the uterus.

Pharmaceutical interest: The pharmacological potential of Labisia pumila (Bl.) F-Vill. & Naves remains unexplored, but it is quite possible that triterpenoid saponins, which are common in the Myrsinaceae, are responsible for the medicinal and especially uterus strengthening properties of this plant. Fig. 140. Labisia pumila (Bl.) Bth. & Hook.

Reference Jamal JA (1999) Investigation of Labisia pumila: A Malay Traditional Herb for Pregnant Women. PhD Thesis. London.

Warning: Extracts of Labisia pumila (Bl.) F-Vill. & Naves promote the growth of endometrial estrogen dependent adenocarcinoma cells of the type Ishikawa var 1 cultured in vitro (Jamal, 1999).

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V. Subclass ROSIDAE Takhtajan 1966 The subclass Rosidae is a large group which consists of 18 orders, 114 families, and about 58 000 species of trees, shrubs, herbs and climbers thought to have originated from the subclass Magnoliidae in the early Upper Cretaceous period (Appendix I). The chemical weapons used by Rosidae, especially the primitive ones, are hydrolyzable tannins inherited from Magnoliidae. Other noticeable secondary metabolites of Rosidae are cyanogen glycosides, triterpenes, alkaloids and iridoids. The leaves of Rosidae are pinnate, serrate, and stipulate. The flowers include a definite number of sepals and petals which are free and inserted in a nectary disc from which several stamens develop, initiating a centripetal sequence. The ovary in Rosidae comprises of 2 to several locules, containing 1 or 2 ovules per locule. Countless plant species from the Rosidae prove to be useful agricultural and pharmaceutical products. The order Rosales is the most archaic order of Rosidae and is a common ancestor to all other orders in this subclass.

A. Order ROSALES Lindley 1833 The order Rosales consists of 24 families and about 6600 species of cosmopolitan plants. The family Rosaceae of approximately 3000 species is by far the largest family in this order, followed by the family Crassulaceae of 900 species and the family Saxifragaceae. The Connaraceae is the oldest family in the Rosales.

1. FAMILY CONNARACEAE R. Brown in Tuckey 1818 nom. conserv., the Connarus Family Physical description: The family Connaraceae consists of about 20 genera and 350 species of tanniferous tropical trees, shrubs and climbers known to abound with tannins and 1,4-benzoquinones (rapanone). The leaves in this family are alternate, without stipules and pinnate. The inflorescences are terminal, pseudoterminal or axillary racemes or panicles. The flowers are hermaphrodite or unisexual, and actinomorphic or slightly zygomorphic. The calyx comprises of 5 coriaceous, free or slightly connate, and imbricate or valvate sepals. The corolla consists of 5 free imbricate petals. The andrecium consists of 5–10 stamens arranged in 2 whorls, with dithecal anthers opening by longitudinal slits. The gynecium is archaic as it consists of 5 free carpels, with only one being fertile, maturing into a dehiscent and often bright red capsule, containing a black or brown, glossy seed embedded in a colorful aril. Pharmaceutical interest: The seeds of Connaraceae are known to be poisonous on account of a series of very unusual amino acids such as

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241

L-methionine sulphoximine (glabrine, cnestine), which causes convulsion and death. The seeds of Rourea glabra mixed with corn mash have been used in tropical America for criminal purposes. About 10 species of the plants classified within the family Connaraceae are medicinal in the Asia-Pacific. These plants are often used to invigorate the uterus and to treat fever. It will be interesting to learn whether a more intensive study on Connaraceae will disclose any molecules of therapeutic interest. Agelaea trinervis (Llanos) Merr. [From Greek, agelios = a herd and tri = 3 and neuron = nerve]

Synonymy: Agelaea wallichii Hook f., Castanola trinervis Llanos, Agelaea cambodiana Pierre, Agelaea wallichii JD Hooker, Castanola glabrifolia Schellenberg, Castalona obliqua Schellenberg.

Physical description: It is a woody climber which grows to a length of 7 m in the primary and secondary rainforests of China, Cambodia, IndoneCommon names: Kalam malam sia, Laos, Malaysia, the Philippines, (Malay); li dou teng (Chinese). Thailand and Vietnam. The wood is reddish and the bark is dark grey. Leaves: 3-foliolate, spiral and without stipules. The rachis is 3 cm–10 cm long. The petiolules are stout. The folioles are coriaceous, elliptic, lanceolate, 6.5 cm–14 cm × 2.7 cm–7.2 cm. The margin is wavy and recurved. The blade shows 3–4 pairs of secondary nerves which are flat above and raised beneath. The inflorescences are axillary and velvety panicles. The flowers are 1 cm × 7 mm, and cream-colored with a red calyx. The fruits are dehiscent, 1 cm long follicles each containing a single seed which is black and glossy, and embedded in a yellow aril (Fig. 141). Uses: In Malaysia, Agelaea trinervis (Llanos) Merr. is used to treat rheumatism and to stimulate venereal desire.

Pharmaceutical interest: The pharmacological potential of this plant and of the genus Agelaea in general is virtually unexplored. It will be interesting

Fig. 141. Agelaea trinervis (Llanos) Merr. From: KLU Herbarium 11675. Flora of Malaya. Field collector and botanical identification: Benjamin C Stone. July 1970. Geographical localization: Pahang, Tasek Bera, low altitude.

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to learn whether a more intensive study on Agelaea species will disclose any 1,4 benzoquinones of chemotherapeutic interest. Warning: Caution must be taken as the toxic effects of this plant are unknown. Cnestis palala (Lour.) Merr. [From Greek, knestis = with irritant hairs] Synonymy: Thysanus palala Lour., Cnestis ramiflora Griffith. Common name: Shi mao guo (Chinese). Uses: In Malaysia, a decoction of the roots of Cnestis palala (Lour.) Merr. is drunk to treat malaria, assuage stomachache, normalize urination, aid recovery from childbirth and to resolve sprains.

Physical description: It is a woody streamside climber found in the rainforests of Hainan, Indonesia, Laos, Malaysia, Burma, Thailand and Viet- Fig. 142. Cnestis palala (Lour.) Merr. From: KLU Herbarium 32429. Field collector: WJJO nam. The wood is reddish and the de Wilde and Wilde- Duyfjes. 5 Aug 1979. bark is brown and fissured longitudi- Geographical localization: Sikundur Forest nally. Leaves: 30 cm–50 cm long, spi- Reserve, c. 75 Km. West Northwest of Medan, ◦  ◦  ral, without stipules, crowded at the c. 3 55 North–98 05 East; 50 m–100 m altiapex of the stem, consisting of up to tude, Besitang road, Km. 14 to Aceh border in recently logged forest. Botanical identification: 14 pairs of folioles. The rachis is vel- M Goh WK, 27 July 1998. vety. The folioles are velvety beneath, oblong, 2.2 cm × 3.8 cm and sessile. The base of the folioles is obscurely cordate, the apex rounded, and the midrib is sunken above and raised beneath. The blade shows up to 10 pairs of secondary nerves. The inflorescences are velvety and emerge all along the stem below the leafy crown. The sepals are red and velvety, and the petals are white, short and notched. The andrecium comprises of 10 stamens which are whitish. The gynecium consists of 5 free carpels (Fig. 142). Pharmaceutical interest: Extracts of Cnestis ferruginea display anticonvulsant and antifungal properties experimentally (Declume C et al., 1984; Le Grand A et al., 1988).

Subclass Rosidae O H3C S HN

243

O OH NH2

L - Methionine sulphoximine

References Declume C, et al. (1984) Annales Pharmaceutiques Fran¸caises 42(1): 35–41. Jeannoda VL, et al. (1984) Biochimie 66(7–8): 557–562. Le Grand A, et al. (1988) J Ethnopharmacol 229 1): 25–31. Murakoshi I, et al. (1993) Chem Pharm Bull 41(2): 388–390.

Warning: The seeds of Cnestis palala (Lour.) Merr. are poisonous on account of L — methionine sulfoximine which has also been isolated from the root bark of Cnestis glabra (Jeannoda VL et al., 1984; Murakoshi I et al., 1993). Connarus monocarpus L. [From Greek, konaros = a spring tree, monos = alone and karpos = fruit] Physical description: It is a small Synonym: Connarus oligophyllus shrub found in the South Asian Wall. rainforest. Leaves: pinnate, consists Common names: Atlaket, kadaktalet, of 3–5. The petiolules are 3 mm– talet (Burmese); lemak lemak 5 mm long. The folioles are glabrous, (Malay), sedippulikkodi (Tamil). 7.5 cm–10 cm × 3.2 cm–4.5 cm, and show 3–5 pairs of secondary nerves. The blade is glossy, and elliptic or elliptic-lanceolate, round or acute at the base and the apex is obtusely acuminate. The flowers are 5 mm long and crowded in upright pyramidal densely pubescent terminal panicles. The flower pedicels are short, stout and articulate. The calyx consists of 5 ovate-oblong, subacute and densely pubescent sepals. The corolla comprises of 5 petals which are much longer than the sepals, linear-oblong and more or less pubescent outFig. 143. Connarus monocarpus L. side. The andrecium comprises of 10 stamens. The gynecium includes 5 pubescent carpels, among which only a single one is perfect.The fruits are free, bright red follicles seated on a persistent but non-accrescent calyx (Fig. 143).

244

Division MAGNOLIOPHYTA OCH3 HO O

O

HO

OH

HO HO

OH

OH

H

H

O

O

O Bergenin

Rapanone

Pharmaceutical interest: One might set Uses: In Malaysia, the pounded the hypothesis that the anti-inflammatory roots are applied externally to property mentioned above could be attrisoothe inflamed areas and a buted to bergenin and leucopelargonidecoction of the bark is drunk to din (Aiyar SN et al., 1963), as well assuage stomachache. In India, a as rapanone. Note that Connarus monodecoction of the bark is used to carpus L. contains rapanone which is treat syphilis and the pulp of the fruit is applied to diseased eyes. anthelmintic, oral contraceptive, antimicrobial and angiotensin-converting enzyme inhibitor (IC50 = 36 µM; Lund AK et al., 1998; Calle J et al., 2000). It will be interesting to learn whether more intensive future research on bergenin will disclose any therapeutic properties. Note that rapanone and bergenin occur also in the family Myrsinaceae. Do Myrsinaceae and Connaraceae share common ancestors in the Magnoliidae? References Aiyar SN, et al. (1963) Phytochem 3(2): 335–339. Calle J, et al. (2000) J Ethnopharmacol 71(3): 521–525. Lund AK, et al. (1998) Phytomed 5(3): 199–203.

Warning: Caution must be taken as the toxic effects of this plant are unknown. Connarus semidecandrus Jack [From Greek, konaros = a spring tree; from Latin, semi = half; and from Greek, deka = ten and andro = male] Physical description: It is a climbing shrub found in Burma, Malaysia and Indonesia. Leaves: alternate, 18 cm– 30 cm long and imparipinnate. The petiolules are 3 mm long. The folioles are coriaceous, oblong or elliptic-lanceolate,

Synonymy: Connarus mutabilis Bl., Connarus neurocalyx Planch. Common names: Akar kuaya, akar tanga burong, akar tukor nyamok, akar tupai tupai (Malay).

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cuneate, at the base and show 6–7 pairs of secondary nerves. The inflorescences are terminal, 15 cm–25 cm long panicles.The calyx consists of 5 sepals which are lanceolate and dotted with red spots. The corolla comprises of 5 lanceolate petals which are blunt and dotted with numerous red spots outside. The fruits are red follicles which are flattened. Each follicle contains a single seed which is glossy, black and embedded in a yellow aril. Pharmaceutical interest: The therapeutic potential of Connarus semidecandrus Jack is awaiting discovery. Benzoquinones are probably involved in the antifebrile property mentioned above.

Uses: In Malaysia, the roots are used to treat fever. In the Philippines, a decoction of the root is ingested to strengthen the uterus.

Warning: Caution must be taken as the toxic effects of this plant are unknown. Rourea minor (Gaertn.) Leenh. [After Aroura in French Guiana and from Latin, minor = less] Synonymy: Rourea erecta (Blco.) Merr., Rourea humilis Bl., Rourea microphylla Planch., Santaloides floridum O. Ktze., Santaloides pulchellum O. Ktze.

Physical description: It is a large woody vine or shrub found in India, Ceylon, South China, and Indonesia. The young stems are hairy. Leaves: simple or pinnate. The petiolules are 2 mm–6 mm long. The folioles are Fig. 144. Rourea minor (Gaertn.) Leenh. 1 cm–25 cm × 5 mm–10 cm. The blade is suborbicular or ovate or lanceolate, and thinly coriaceous, acuminate at the apex and acute or cordate at the base. The folioles show 4–10 pairs of secondary nerves. The inflorescences are 20 cm long racemes which are laxly branched, multi-flowered and glabrous. The calyx consists of 5 sepals which are 2 mm–4 mm long. The corolla consists of 5 petals which are 4 mm–7.5 mm long. The fruits are oblique-ovoid and 1 cm–3 cm × 3 mm–10 mm follicles (Fig. 144).

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Pharmaceutical interest: L-Methionine sulphoximine: A comUses: In Malaysia, a decoction of the mon poison found in the Connaraceae roots is drunk to treat fever, and the and probably in Rourea minor (Gaertn.) pounded roots are drunk to heal Leenh. is L-methionine sulphoximine sores. In the Philippines, a decoction which (Jeannoda VL et al., 1985). of the roots is used to invigorate the The mode of action of L-Methionine uterus, expel impurities, induce vomit sulphoximine is based on the fact that it and to kill wild dogs. is shaped like L-glutamic acid (an excitatory amino acid) and acts as a false substrate for glutamine synthetase, which normally converts glutamic acid into glutamine. Glutamic acid accumulates in neurons and causes a continuous depolarization of dendrites, hence resulting in central nervous system disturbances and convulsions. L-Methionine sulphoximine lowers extracellular potassium during acute hyperammonaemia (Sugimoto H et al., 1997). O H3C S HN

O

O OH

NH2 L - Methionine sulphoximine

O

HO

OH NH2 Glutamic acid

References Jeannoda VL, et al. (1985) J Ethnopharmacol 14(1): 11–17. Sugimoto H, et al. (1997) J Cereb Blood Flow Metab 17: 44–49.

Warning: Caution must be taken as the toxic effects of this plant are unknown. Roureopsis emarginata (Jack) Merr. [After Aroura in French Guiana and from Latin, marginata = margined] Physical description: It is a woody Synonymy: Roureopsis pubinervis climber that grows in the rainforests of Planch. Burma, Malaysia and South China. The wood is yellowish-red and the bark is blackish. Leaves: imparipinnate, spiral, without stipules and consist of 4–6 pairs of folioles, including a terminal one. The rachis is 1.5 cm–7 cm long. The petiolules are indistinct. The folioles are lanceolate, 2.8 cm–3.2 cm × 8 cm–1.1 cm, and acute at the

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247

base. The apex extends into a 1 cm long tail. The secondary nerves are inconspicuous.The inflorescences are axillary racemes. The fruits are dehiscent, 2.4 cm × 8 cm bright red follicles, each containing each a single seed (Fig. 145). Uses: In Malaysia, the leaves of Roureopsis emarginata (Jack) Merr. are applied externally to treat fever and to assuage pain.

Pharmaceutical interest: The pharmacological properties of Roureopsis emarginata (Jack) Merr. are unknown. Antidiarrheal and antimicrobial properties are established from the extracts of Roureopsis obliquifoliata (Longanga O et al., 2001; Otshudi AL et al., 2000). Are tannins or benzoquinones involved as well?

Fig. 145. Roureopsis emarginata (Jack) Merr. From: KLU Herbarium 32356. Field collectors: WJJO de Wilde & BEE de Wilde - Duyfjes. 5 Aug 1979. Geographical localization: Sikundur Forest Reserve, c. 75 Km. West Northwest of Medan, c. 3◦ 55 North–98◦ 05 East; 50 m– 100 m alt., Besitang road, Km 14 to Aceh border in recently logged forest. Botanical identification: M Goh WK, 27 Jul 1998.

References Longanga O, et al. (2001) Fitoter 72(3): 291–294. Otshudi AL, et al. (2000) Phytomedicine 7(2): 167–172.

Warning: Caution must be taken as the toxic effects of this plant are unknown.

2. Family CUNONIACEAE R. Brown. in Flinders 1814 nom. conserv., the Cunonia Family Physical description: The family Cunoniaceae consists of 25 genera and 350 species of shrubs and trees, mostly native to the Southern Hemisphere. Cunoniaceae abound with tannins, proanthocyanins, ellagic acid and aluminum. The leaves of Cunoniaceae are pinnate and opposite. The folioles are serrate and the stipules are present and interpetiolar. The inflorescences are racemes or panicles. The flowers are small, regular, perfect, and hypogynous. The calyx consists of 4–5 free sepals and the petals are alternate, as numerous as, and smaller than the sepals. The andrecium comprises of 8–11

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stamens, with versatile, inverted, tetrasporangiate, dithecal stamens opening by longitudinal slits. A nectary disc is present. The gynecium consists of 2–5 carpels, united in a plurilocular, superior ovary with independent styles, each locule enclosing 2 to several ovules attached on the axile or apical placentas. The fruits are capsular and contain several seeds which are small, winged or hairy. Pharmaceutical interest: Very little is so far known about the pharmacological potential of Cunoniaceae. It will be interesting to learn whether a more intensive study on Cunoniaceae will disclose any tannins of therapeutic interest. Weinmannia blumei Planch. is used for medicinal purposes in Indonesia. Weinmannia blumei Planch. [After JW Weinmann, a German herbalist of the 17th century and after Carl Ludwig von Blumen, early 18th century taxonomist] Synonymy: Weinmannia ledermannii Schlechter, Weinmannia papuana Schlechter, Weinmannia sundana Miq. Common names: Malayan mountain ash, ki ringgit (Indonesian); sumu silan (Malay). Uses: Indonesians use the bark of Weinmannia blumei Planch. as an astringent remedy. The pharmacological potential of this plant is unexplored. Note that honeys of Weinmannia racemosa contain unusual terpenes.

Physical description: It is a tree which grows to a height of 12 m in the rain- Fig. 146. Weinmannia blumei Planch. From: KLU 23704. Flora of Malaya. Herbarium Ausforests of Malaysia and Indonesia. The traliense C.S.I.R.O, Canberra, A.C.T. (CANB). stems are smooth, lenticelled, some- Field collector and botanical identification.: what articulate, and dark brown. The RD Hoogland. 27 Mar 1975. Geographiwood is reddish-brown. Leaves: sim- cal Localization: common in forest on steep ple, decussate and stipulate. The stip- slope, altitude: 3700 ft. Bukit Fraser, along Road from the Gap, Selangor, Malaysia. ules are interpetiolar, kidney-shaped, 9 mm × 5 mm–2.3 cm × 1.5 cm, and leathery. The rachis is somewhat articulate, 7 cm–11.3 cm long and microscopically hairy. The folioles are

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249

sessile, opposite, lanceolate, serrate, asymmetrical, leathery, 1.1 cm–3.5 cm× 4 cm–12 cm, and smaller toward the base of the rachis. The midrib is sunken above and raised below, and the secondary nerves are about a dozen. The inflorescences are pinkish, profusely blooming and showy. The calyx comprises of 4 sepals which are 1 mm long, hairy at the base and orbicular. The petals are 1 cm × 5 mm and glabrous. The andrecium is showy and comprises of 8 stamens, among which a few are aborted (Fig. 146). References Broom JS, et al. (1992) Tetrahedron Letter 33(41): 6201–6204. Ede ME, et al. (1993) Tetrahedron Letter 34(42): 6795–6798.

Warning: Caution must be taken as the toxic effects of this plant are unknown.

3. Family PITTOSPORACEAE R. Brown in Flinders 1814 nom conserv., the Pittosporum Family Physical description: The family Pittosporaceae consists of 9 genera and 200 species of shrubs and small trees that are widely distributed in the tropical and warm temperate parts of the world, especially in Australia. The array of chemical repellents in Pittosporaceae is broad and includes triterpenoid saponins, essential oils, polyacetylenic fatty acids, and proanthocyanins. About 150 species of Pittosoraceae belong to the single genus Pittosporum. The leaves of Pittosporaceae are simple, alternate, leathery, glossy, and without stipules. The inflorescences are axillary, cymose or racemose. The flowers are perfect, regular, hypogynous and pentamerous. The stamens alternate with the petals. The gynecium consists of 2–5 carpels united to form a compound, unilocular ovary with a single style and a capitate stigma. The ovary encloses numerous ovules attached to parietal placentas. The fruits are dehiscent capsules or berries. The seeds are often embedded in a viscous pulp and include a succulent, oily and proteinaceous endosperm. Pharmaceutical interest: A classical example of Pittosporaceae is Pittosporum tobira (Thunb.) Ait. (Australian laurel) which is cultivated as an ornamental evergreen shrub. Pittosporum tobira (Thunb.) Ait., Pittosporum ferrugineum Ait., Pittosporum pentandrum (Blco.) Merr. and Pittosporum resiniferum Hesm. are used for medicinal purposes in the Asia-Pacific. To date, the pharmacological potential of the family Pittosporaceae remains unexplored.

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Pittosporum tobira (Thunb.) Ait. [From Greek, pitta = resin and spora = seed and from Japanese, tobira = Pittosporum tobira (Thunb.) Ait.] Common names: Australian laurel, mock orange, Japanese Pittosporum; hai tong (Chinese).

Physical description: The plant is native to Japan and China. The stems are terete, smooth and glabrous. Leaves: simple, alternate, crowded at the apex of the stems and without stipules. The petiole is 6 mm–1.5 cm long and channeled above. The blade is spathulate, coriaceous, 6 cm×2.8 cm– 12 cm × 4 cm, glossy, and dark green. The margin of the blade is wavy and Fig. 147. Pittosporum tobira (Thunb.) Ait. recurved, and the midrib is deeply From: KLU Herbarium 037870. Ex. Herbarsunken above and raised below. The ium of University of the Ryukyus. Geographblade shows 7–9 pairs of secondary ical Localization: Okinawa: Yona Experim. nerves. The inflorescences are 2.5 cm Plantation of the Univ., Kunigami; along woodland path. 7 June 1984. Field Collector and long axillary racemes of whitish flow- Botanical Identification: Shimabuku. From: KLU ers. The corolla is tubular and 5-lobed. 10418. Chiba, 30 Sep 1955. The andrecium consists of 5 stamens alternating with the lobes. The fruits are capsular, 3-lobed, green, 1.5 cm × 1.3 cm, and dehiscent. The seeds are numerous and embedded in a viscous and bright red pulp (Fig. 147). Pharmaceutical interest: An ethanol extract of the leaves of Pittosporum phylliraeoides DC. var. microcarpa S. Moore is antiviral against Ross River virus cultured in vitro (Semple SJ et al., 1998).

Uses: In China, Pittosporum tobira (Thunb.) Ait. is used to stop dysentery, treat rheumatism and to strengthen dentition.

Reference Semple SJ, et al. (1998) J Ethnopharmacol 60(2): 163–172.

Warning: Pittosporum tobira (Thunb.) Ait. is toxic.

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251

4. Family CRASSULACEAE A. P. de Candolle in Lamarck & de Candolle 1805 nom. conserv., the Stonecrop Family Physical description: The family O Crassulaceae consists of 25 genera O and 900 species of perennial herbs N N found predominantly in the Northern H Hygrine Pelletierine Hemisphere and in Southern Africa. Crassulaceae have the tendency to accumulate water to survive in dry O OH habitats. These plants are succulent N and abound with tannins, oxalic acid, and an interesting series of piperidine alkaloids (Sedum, Fig. 148). The Sedinone leaves in this family are simple, entire, without stipules, alternate, and oppo- Fig. 148. Alkaloids from some Asian Sedum site or whorled.The inflorescences are species. cymose or solitary. The flowers are bisexual, actinomorphic, and comprise of 4–5 sepals which are free or united into a tube. The corolla consists of 4–5, free or variously connate, and hypogynous petals. The andrecium consists of 4–10 stamens, the anthers of which are 2-celled, introrse and open longitudinally. The gynecium consists of 4–5 carpels which are free or slightly united. Each carpel is marked with a characteristic nectariferous appendage at the base and encloses several ovules attached to submarginal placentas. The fruits are free follicles containing several small seeds. Pharmaceutical interest: Cotyledon umbilicus (Umbilicus pendulinus de Cand.), Sempervivum arboreum L. (Sempervivum africanum Mill.) and Sempervivum tectorium L. have been used as counter-irritants in Western medicine since a very remote period in time. The counter-irritancy of Crassulaceae is attributed to crystals of oxalic acid which irritate the skin and mucosa. It will be interesting to learn whether a more intensive study on Crassulaceae will disclose any neuroactive piperidine alkaloids of therapeutic interest. In the AsiaPacific, about 10 species of plants classified within the family Crassulaceae are of medicinal value and often used as counter-irritant remedies. Kalanchoe laciniata (L.) DC [From Chinese, kalanchoe = Chinese name of Kalanchoe species and from Latin, lacinia = lappet] Physical description: It is a herb which grows to a height of 90 cm–1.2 m in tropical Asia and Africa. The plant is ornamental and naturalized in several

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Common names: Joubarbe (French); setawar kampong (Malay); siemprevica (Filipino); hemasaraga (Sanskrit); malakalli (Tamil); nien to (Cambodia, Laos, Vietnamese).

tropical countries. The stems are succulent, glabrous, and slightly branched. Leaves: simple, without stipules and 7.5 cm–10 cm long. The petiole is 2.5 cm–3.8 cm long, flattened above, succulent and amplexicaul. The blade is serrate, crenate or entire, glossy and pale glaucous. The inflorescences are paniculate cymes. The calyx is 3 mm– 5 mm long and develops 4 lanceolate lobes. The corolla comprises of 4 orange petals which are lanceolate, acute or acuminate, glabrous or pubescent. A few hypogynous scales of 3 mm–4 mm are present. The fruits are 8 mm long follicles which are ventrally dehiscent.

Uses: The crushed leaves of Kalanchoe laciniata (L.) DC. are used to make counter-irritant remedies all over Asia. In Malaysia, a poultice of the powdered leaves is used to soothe inflammation, heal boils and wounds, and to treat cough and smallpox. Kalanchoe laciniata (L.) DC. mixed with Andrographis paniculata Nees is used to treat infected fingers. A decoction of the whole plant is drunk to assuage gastric pain and to treat heart discomfort. In India, the crushed leaves are applied to wounds, and used to soothe inflammation. The juice expressed from the leaves is drunk to treat bilious diarrhea and lithiasis. In the Philippines, the crushed leaves are used to assuage headache. In Cambodia, Laos, and Vietnam, the crushed leaves are applied externally to reduce body temperature and to heal ulcers.

Pharmaceutical interest: The counter-irritant property of Kalanchoe laciniata (L.) DC. is attributed to crystals of oxalic acid which irritate the skin. A number of plants classified within the genus Kalanchoe display antibacterial (Supteli EA et al., 1980) and antiviral (Shirobokov VP et al., 1981) properties in vitro but what are the principles involved? References Masvingwe C, et al. (1997) J S Afr Vet Assoc 68(1): 18–20. Shirobokov VP, et al. (1981) Antibiotiki 26(12): 897–900. Supteli EA, et al. (1980) Mikrobiol Zh 42(1): 86–90.

Warning: Note that if ingested in excess, oxalic acid sequesters calcium, precipitates and obstructs the nephrons, hence causing renal failure. Other poisonous principles of Kalanchoe species are bufadienolides which are cardiotoxic (Masvingwe C et al., 1997). Kalanchoe pinnata (Lamk.) Pers [From Chinese, kalanchoe = Chinese name of Kalanchoe species and from Latin, pinnatus = feathered]

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253

Physical description: It is a herb Synonymy: Bryophyllum calycinum which grows to a height of 30 m– Salisb. 1.2 m. The plant is native to tropiCommon names: Yoekiyapinba cal Africa and naturalized in several (Burmese); gros pourpier clochette countries. The stems are obtusely 4(French); sedingin (Malay); parnabija angled, succulent, glabrous, and the (Sanskrit); malaikalli (Tamil). younger parts are reddish with white dots. Leaves: simple, without stipules, Uses: Kalanchoe pinnata (Lamk.) and decussate. The blade is ovoid, Pers. is counter-irritant. In Malaysia, spoon-shaped, and the margin is crethe juice expressed from this plant is nate. The flowers are pendulous, and mixed with honey and used to treat tonarranged in large spreading panicles. sillitis, mastitis, earache, inflammation The pedicels are slender. The calyx is and haemoptysis. In India, the bark is 2.5 cm–3.8 cm long, penciled with red used to stop diarrhea, flatulence and lines, green at the base, pale green vomiting, assuage pain and to counabove, and develops 4 triangular lobes. teract snake-and scorpion-poisoning. The corolla is swollen and octagonal The leaves are applied externally to at the base, constricted in the middle, heal wounds and boils, and the plant reddish purple, and develops 4 triis used to treat jaundice. In Cambodia, Laos, and Vietnam, a paste made from angular lobes. The anthers are hasthe powdered leaves is used to heal tate and black, and the filaments are burns and to soothe scalds. green at the base and pinkish below the anthers. Hypogynous scales subquadrate, free or adherent to the carpels are present. The fruits are follicles enclosed in the vestigial perianth which is papery. The seeds are small (Fig. 148). Pharmaceutical interest: Anti-inflammatory property: The juice given orally at a dose of 4 mL/Kg, protects guinea-pigs from death by asphyxia caused by 5 mg of histamine suggesting an anti-histaminic effect (Nassis CS et al., 1992). Kalanchoe pinnata Pers. inhibits T-cell-mediated responses such as the mixed leukocyte reaction and the delayed type hypersensitivity reaction on account of the fatty acid mixtures of palmitic acid, stearic acid of arachidonic and behenic acids (Moraes VL et al., 2000). Other properties: An extract of leaves given orally at 8 mg per day protects

Fig. 148. (a) Kalanchoe pinnata (Lamk.) Pers.

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Division MAGNOLIOPHYTA

BALB/c mice against Leishmania amazonensis (Da Silva SAG et al., 1995). Bufadienolides of Kalanchoe pinnata (Lamk.) Pers. inhibits 12-Otetradecanoylphorbol-13-acetate (TPA)-induced early expression of the Epstein-Barr Virus by Raji cells (Supratman U et al., 2001). The hepatoprotective property of Kalanchoe pinnata (Lamk.) Pers. is confirmed as the juice of the leaves protects rats against carbon tetrachloride-induced hepatotoxicity (Yadav NP et al., 2003). References Da Silva SAG, et al. (1995) Acta Tropica 60(3): 201–210. Moraes VL, et al. (2000) Planta Med 66(2): 134–137. Nassis CS, et al. (1992) Braz J Med Biol Res 25(9): 929–936. Supratman U, et al. (2001) Biosc Biotechnol Biochem 65(4): 947–949. Yadav NP, et al. (2003) J Ethnopharmacol 86(2–3): 197–202.

Warning: Kalanchoe pinnata (Lamk.) Pers. is toxic. Sedum alfredi Hance [From Latin, Sedum = sedentary] Synonymy: Sedum morrisonense Hay., Sedum formosum.

Physical description: It is a perennial seashore herb found in China and Taiwan which grows to a height of 15 cm. The stems are dichotomous and succulent. Leaves: simple, without stipules, and alternate or opposite. The blade is obovate to nearly orbicular, and 1.5 cm–2.2 cm×8 mm–1.2 cm. The apex of the blade is broadly round and the base cuneate. The inflorescences are multiflowered and 5 cm– 8 cm long cymes. The flowers are sessile, 1 cm long, yellow and show a few Fig. 149. Sedum alfredi Hance. leaf-like bracts. The calyx consists of 5 sepals which are 2 mm–3 mm long, asymmetrical and linear-lanceolate. The corolla consists of 5 petals which are lanceolate, 6 mm–7 mm long and acuminate. The stamens are shorter than the petals. The gynecium consists of

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independent carpels, the fertile ones being upright, lanceolate, 5 mm–6 mm long and terminated by a 1 mm style at the apex. The fruits are follicles containing many seeds (Fig. 149). Pharmaceutical potential: The pharUses: In China and Taiwan, a paste macological potential of Sedum alfredi of Sedum alfredi Hance is used is to date unknown but one might have externally to heal burns and wounds. a closer look at it as a crude alkaloid fraction of Sedum sarmentosum Bunge at various doses (50 µg/mL– 150 µg/mL) for 24 or 48 h. inhibits dose-dependently the survival of murine hepatoma (BNL CL.2) and human hepatoma (HepG2) cells cultured in vitro (Kang TH et al., 2000). In addition, a carbohydrate characterized from Sedum spectabile when condensed with acetone (helotylphin), destroys duck’s Hepatitis B Virus and modulates immunity. Note that a number of polysaccharides characterized from Sedum telephium display anti-inflammatory and anticomplementary properties experimentally (Sendl A et al., 1993). In general, Oligosaccharides and polysaccharides of the Sedum species and Crassulaceae may hide a stock house of pharmacological activities, but this has yet to be confirmed. References Kang TH, et al. (2000) J Ethnopharmacol 70 (2000) 177–182. Sendl A, et al. (1993) Phytochem 34(5): 1357–1362.

Warning: Caution must be taken as the toxic effects of this plant are unknown. Sedum bulbiferum Mak. [From Latin, Sedum = sedentary and bolbos = onion and ferre = to bear] Physical description: It is a small and Synonymy: Sedum alfredi var. succulent herb found in China, Korea and bulbiferum (Mak.) Frod. Japan. The stems are glabrous and the Common names: Bulbiferous internodes are rooting. Leaves: simple, Stonecrop; komochi mannengusa spiral, sessile, opposite and without stip(Japanese). ules. The blade is spathulate, 8 mm × 3 mm–1.5 cm × 5 mm, round at the apex and tapered at the base. The margin is serrulate with very small translucent scales. The inflorescences are terminal and axillary. The flowers are small and yellow. The fruits are translucent follicles (Fig. 150).

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Uses: In China, Sedum bulbiferum Mak. is used externally to treat burns.

Pharmaceutical potential: The pharmacological potential of Sedum bulbiferum Mak. remains unexplored til to date. The plant is however known to contain pelletierine (Henk T et al., 1996), a piperidine alkaloid also found in Punica granatum L. which has a specific action on tapeworms. Preparations from Punica granatum L. (family Punicaceae, order Myrtales, and subclass Rosidae) were used in Western medicine (British Pharmaceutical Codex, 1911) in doses of 3 to 5 decigrams to expel worms from the intestines.

Fig. 150. Sedum bulbiferum Mak. From: Ex. Herbario Universitatis Tokyoensis. Geographical localization: Japan, Honshu: Gunma Pref., Hujioka-shi, Nakajima; 25 June 1973. Field collector and botanical identification: Hideaki Ohba 73601.

Reference Henk T, et al. (1996) Phytochem 41(5): 1319–1324.

Warning: Caution must be taken as the toxic effects of this plant are unknown.

B. Order FABALES Bromhead 1838 The order Fabales consists of 3 families and about 14 000 species of trees, shrubs, herbs and climbers thought to have originated from the order Rosales near the Connaraceae (Appendix I). In terms of the number of species, it is the largest group in the Rosidae and one of the largest in Magnoliopsida. Fabales are chemically diverse but often endowed with tannins, gums, several sorts of phenolic compounds, and several series of pyridine, pyrrolizidine, indole and quinozilidine alkaloids inherited from the Magnoliales via the Rosales.The flowers of Fabales are actinomorphic (family Mimosaceae) or zygomorphic (family Caesalpiniaceae and family Fabaceae) and comprises of a corolla of 5 petals. The petals are valvate (family Mimosaceae) or imbricate with the adaxial one overlapped by a pair of lateral petals (family Caesalpiniaceae) or imbricate with the adaxial petal overlapping the lateral petals (family Fabaceae). The fruits are pods. The seeds are starchy and oily, containing galactomannans

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(polysaccharides of D-mannose and D-galactose), toxic non-protein amino acids, steroids and lectins (glycoproteins). Belonging to the order Fabales, are several medicinal plants, countless agricultural products and stock houses of poisonous plants. About 100 plant species in the Fabales are used for medicinal purposes in the Asia-Pacific. Note that most of these plants are used for their astringency.

1. Family MIMOSACEAE R. Brown in Flinders 1814 nom. conserv., the Mimosa Family Physical description:The family Mimosaceae consists of 40 genera and about 2000 species of trees and shrubs but rarely herbs, which are often prickly. Mimosaceae are known to abound with tannins, mucilages, gums, and an unusual series of amino acids. The leaves of Mimosaceae are bipinnate and stipulate. The flowers are hermaphrodite, small, spicate, racemose or capitate, and actinomorphic. The calyx is tubular, valvate, and 5-lobed. The petals are small, valvate, free or connate, and hypogynous. The stamens are numerous, free or monadelphous, and often conspicuous. The anthers are small, 2-celled, open lengthwise, and marked with a deciduous gland at the apex. The gynecium consists of a single carpel forming a superior and single-locular ovary which encloses 2 to several ovaries attached to marginal placentas. The fruits are pods. The seeds are often glossy. Pharmaceutical interest: Examples of Mimosaceae of economic value are Acacia senegal Willd. (Arabic gum), Entada gigas (L.) Fawc. and Rendle (cacoon), Propsopis juliflora DC. (mesquit tree), Acacia melanoxylon R. Br. (Australian blackwood) and Xylia dolabriformis Benth. (ironwood). It will be interesting to learn whether a more intensive study on Mimosaceae will disclose any molecules of therapeutic interest. Acacia farnesiana (L.) Willd [From Latin, acacia = thorny and after 17th century Roman Cardinal Alessandro Farnese]

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Synonymy: Mimosa farnesiana L. Common name: Sponge tree; acacia odorant (French); nanlonkyaing (Burmese); keo ta (Vietnamese); lasana (Malay); arimeda (Sanskrit).

Physical description: It is an upright, multibranched, prickly tropical shrub native to tropical America which grows to a height of 4 m. Leaves: bipinnate and 5 cm–8 cm long, and comprise of 4–8 pairs of pinnae, each bearing 10–20 pairs of linear oblong and 4 mm–7 mm long folioles. The flowers are very small, fragrant, yellow and arranged in pedunculate, axillary, subglobose heads. The andrecium is showy and comprises of several stamens. The fruits are lanceolate, cylindrical, and 5 cm–7 cm × 1 cm–1.5 cm pods containing several seeds which are compressed and elliptic (Fig. 151).

Uses: In Burma, a paste of the root is used to expel parasites. In Indonesia, the plant is used to induce vomiting. In Malaysia, an infusion of the flowers and leaves is drunk to aid recovery from childbirth. The pounded roots are applied to the swollen parts. In the Philippines, a decoction of the bark is used to treat a prolapsed rectum and leucorrhea. A decoction of the leaves is used to heal ulcers and wounds. In Vietnam, the crushed leaves are applied to heal ulcers and to soothe inflammation. In India, the gum is used to stimulate venereal desire and the bark is used to heal ulcers and to soothe inflammation. Cassie perfume is distilled from the flowers.

Pharmaceutical interest: It is quite probable that most of the medicinal properties mentioned above are attributed to tannins. The anti-inflammatory and antiseptic properties of Acacia farnesiana (L.) Willd are confirmed experimentally: extracts of this plant inhibit moderately the proliferaFig. 151. Acacia farnesiana (L.) Willd. tion of Clostridium perfringens (Sotohy SA et al., 1995) and reduce inflammation in animals (Trivedi CP et al., 1986). References Sotohy SA, et al. (1995) DTW Dtsch Tierarz H Wochenschr 102(9): 344–348. Trivedi CP, et al. (1986) Indian J Physiol Pharmacol 30(3): 267–268.

Warning: Caution must be taken as the toxic effects of this plant are unknown.

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Adenanthera pavonina L. [From Greek, aden = acorn and from Latin, pavoninus = peacok] Common names: Red wood tree; Circassian seeds tree; saga (Malay); bois noir rouge, crete ˆ de paon (French); kanduri batang (Malay); alalangat (Filipino), sem (Tamil).

Physical description: It is a tree native to tropical Asia and Africa.The wood is used in cabinetry and is a source of red dye. Leaves: bipinnate, and stipulate and consist of 7– 13 folioles. The folioles are oblong or ovate, 2.5 cm–4.5 cm × 1.5 cm–2.4cm, obtuse and glabrous. The flowers are whitish and arranged into a spike-shaped raceme. The calyx is cup-shaped and deeply 5-lobed. The corolla consists of 5 lanceolate petals. The andrecium comprises of 10 stamens. The fruits are falcate, 12 cm long pods containing several discoid seeds which are red and glossy (Fig. 152). Pharmaceutical interest: To date not much is known about the pharmacological potential of Adenanthera pavonina L. The plant contains steroidal saponins and flavonoids (Misra G et al., 1975; Gennaro A et al., 1972). The seeds contain trypsin inhibitor proteins (Richardson M et al., 1986).

Fig. 152. Adenanthera pavonina L.

Uses: In Burma, a paste made from the seeds of Adenanthera pavonina L. is applied externally. In Malaysia, the leaves are used to invigorate health. In India, a decoction of the leaves is used externally to treat chronic rheumatism, gout and impotence, and to treat bleeding. The seeds are used in necklaces.

References Gennaro A, et al. Phytochem 11(4): 1515. Misra G, et al. (1975) Planta Med 23(2): 145–142. Richardson M, et al. (1986) Biochimica et Biophysica Acta (BBA)-Protein Structure and Molecular Enzymology 872(1–2): 134–140.

Warning: Caution must be taken as the toxic effects of this plant are unknown.

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Entada phaseoloides (L.) Merr. [From Malabari, entada = Entada phaseoloides (L.) Merr. and from Latin, phaseoloides = bean-like] Physical description: It is a very stout, tropical, woody climber native to Asia. Leaves: bipinnate, stipulate and 20 cm–30 cm long. The rachis ends in a tendril and shows 2 pairs of folioles per pinnae. The folioles are oblong or obovate, 2.5 cm–7 cm × 3 cm–4 cm long and coriaceous. The flowers are very small and arranged in an axillary Synonymy: Entada scandens (L.) and 15 cm long spikes. The calyx Bth., Lens phaseoloides L., Entada is campanulate. The corolla consists koshunensis H. & K. of 5 long equal narrow lobes. The andrecium comprises of 10 stamens. Common names: Giant rattle, lady nut; St Thomas bean, tupe; beluru (Malay); The ovary is subsessile and contains calibeau (French); gannyin (Burmese); many ovules. The style is filiform and day bam bam (Vietnamese), gandoh the stigma concave. The pods are (Javanese); gogo (Filipino); enormous, 35 cm–1.2 m×7 cm–8 cm, heavy, woody, and strongly constricted between each seed. The Uses: In Burma, the seeds of Entada seeds are compressed, glossy, woody phaseoloides (L.) Merr. are used to treat fever. In China, the seeds are and 5 cm × 3 cm × 8 mm (Fig. 153). used to heal hemorrhoids. In Indonesia, The seeds floated across the Atlantic the roasted seeds are used to expel Ocean and washed up on to the impurities after childbirth, assuage shores of Northwestern Europe.

Fig. 153. Entada phaseoloides (L.) Merr.

stomachache, and induce vomiting. The juice expressed from the stems is used to stop dysentery. In India, the seeds are used to aid recovery from childbirth, soothe inflammation, assuage pain in the loins and induce vomiting. In Malaysia, the pods are burned and the ash obtained is applied to the abdomen to treat internal discomfort. Pieces of sun-dried bark are macerated in water and the liquid obtained is used to wash the hair, heal wounds, and treat ptyriasis and irritated skin. In the Philippines, a decoction of the roots is used to reduce abdomen rigidity. The seeds are pulped and applied to the abdomen to assuage colic. An infusion of the bark is used to treat infected skin. In Vietnam, the seeds are used to counteract poison, and to induce stupor and vomiting.

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Pharmaceutical uses: Antipyretic property: The antifebrile and anti-inflammatory properties mentioned above could be partially attributed to entadamide A and B, which inhibit experimentally the enzymatic activity of 5-lipo-oxygenase of RBL-1 cells at 10−4 g/mL (Ikegami F et al., 1989). 5-Lipo-oxygenase is a key enzyme in the synthesis of autacoids at the very beginning of the inflammatory process. Antiseptic property: In regard to the antiseptic property mentioned above, one might think of tannins. The different mechanisms proposed so far to explain tannin antimicrobial activity include the inhibition of extracellular microbial enzymes, deprivation of the substrates required for microbial growth or direct action on microbial metabolism through the inhibition of oxidative phosphorylation (Scalbert A et al., 1991). Antiparasitic properties: A butanolic fraction of the bark of Entada phaseoloides (L.) Merr. inhibits the proliferation of Oncomelania quadrasi cultured in vitro with LC50 values ranging from 3.6 ppm to 3.8 ppm (Yasuraoka K et al., 1977). Entada abyssinica, used in Africa to treat sleeping sickness, contains a clerodane diterpene which inhibits significantly the proliferation of Trypanozoma brucei rhodesiense cultured in vitro (Freiburhans F et al., 1998). It will be interesting to learn whether further studies on Entada phaseoloides (L.) Merr. will disclose any clerodane diterpenes of chemotherapeutic interest. References Freiburghans F, et al. (1998) J Ethnopharmacol 61(3): 179–183. Ikegami F, et al. (1989) Chem Pharm Bull 37(7): 1932–1933. Scalbert A, et al. (1991) Phytochem 30(12): 3875–3883. Yasuraoka K, et al. (1977) Jpn J Exp Med 47(6): 483–487.

Warning: Entada phaseoloides (L.) Merr. is toxic. Leucaena leucocephala (Lamk.) de Wit [From Greek, leukos = white and kephale = head] Physical description: It is a small tree Synonymy: Leucaena glauca sensu native to tropical America. Leaves: bipBth., Mimosa glauca L. innate, stipulate and consists of 4–8 pinnae, and 10–20 pairs of folioles. Common names: Lead tree, white popinac; petai cina, petai jawa The folioles are oblong to lanceolate, (Malay); Santa Helena (Filipino). 7 mm–12 mm long, and glaucous below. A petiolar gland is usually present on the first pinnae of the petiole. The flowers are white and organized in dense, globose, solitary, and long pediceled axillary heads which are

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2 cm–5 cm in diameter. The calyx is 5-lobed. The corolla consists of 5 narrow petals. The andrecium comprises of 10 conspicuous stamens. The fruits are linear pods, which are membranaceous, flat, acuminate, 12 cm × 1 cm–18 cm × 1.5 cm and arranged in conspicuous bunches. Each pod contains 10–20 little seeds which are glossy and brown (Figs. 154 & 155). Uses: In Burma, a paste made from the leaves of Leucaena leucocephala (Lamk.) de Wit is applied externally as an antidote for snake and insect bites. In Indonesia, the seeds are eaten to remove worms from the intestines and to treat diabetes. The leaves, pods and seeds are considered edible there. In Malaysia, a decoction of the seeds is drunk to expel intestinal worms, and to treat diabetes and hypertension. Malays and Filipinos drink a decoction of the roots to induce menses. In Taiwan, this plant is used as fodder. In India, the bark is used to assuage internal pain.

Fig. 154. de Wit.

Leucaena leucocephala (Lamk.)

Pharmaceutical interest: The widespread use of Leucaena leucocephala (Lamk.) de Wit as a tropical forage crop on account of its resistance and richness in protein, vitamin K and carotene, has been partly hampered because of the high amounts of mimosine it is abound with. Mimosine: Mimosine is a non-protein amino acid (N-(3-alanyl)-3-hydroxy-4pyridone) derived from lysine, which is responsible for the toxicity of several plants classified within the genera Mimosa and Leucaena. Fig. 155. Leucaena leucocephala (Lamk.) Mimosine reversibly blocks cell cycle de Wit.

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Fig. 156. Hypothetical mechanism of action by which mimosine blocks cell progression in G1: Mimosine added to the culture medium chelates iron in the medium which is therefore prevented from entering the cell (1). The rest of the mimosine enters the cell where it either binds to a mimosine binding protein (MBP) or chelates intracellular iron from iron-containing proteins such as ribonucleotide reductase (RR). The catalysis of the reduction (deoxygenation) of the ribose ring of ribonucleoside 5 -diphosphates (R5D) to yield 2 -deoxyribonucleoside 5 -diphosphates (2DR5D) in nucleotides by ribonucleotide reductase is inhibited because of iron chelating by mimosine, hence blockage of cell division.

progression in mammalian cells cultured in vitro in phase G1 and is used as a synchronization agent. The precise mechanism by which mimosine disrupts cellular proliferation remains controversial, and it has also been suggested that it blocks cell cycle progression by chelating iron (Fe2+ ) from iron-dependent enzymes such as ribonucleotide reductase (Kulp KS et al., 1996; Fig. 156). A single intragastric dose of mimosine to mice inhibits the intake of iodine 125 by the thyroid at the iodine-binding step (Hegarty MP et al., 1979). References Hegarty MP, et al. (1979) Aust J Biol Sci 32(1): 27–40. Kulp KS, et al. (1996) Toxicology and Applied Pharmacology 139: 356–364. P, et al. (1979) Aust J Biol Sci 32(1): 27–40. Hughes JA, et al. (1996) Exp Cell Res 222(2): 275–280. Holmes JH, et al. (1981) Aust Vet J 57(6): 257–261. Vestena S, et al. (2001) Plant Science 161: 597–604.

Warning: Mimosine ranging from 2% to 10% of diet induce in cattle cataract, goiter, lingual epithelial ulcerations, gingival atrophy, and follicular hyperplasia of the thyroid and teratogenicity (Vestena S et al., 2001; Holmes JH et al., 1981).

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Mimosa pudica L. [From Greek, mimos = mime and from Latin, pudere = be ashamed] Physical description: It is a poisonous, handsome, decumbent tropical herb native to South America. The stems are purplish, woody and prickly. Leaves: bipinnate, 2 cm–5 cm long and automatically closing after being touched. The folioles are numerous (5–26 pairs), 6 mm–1.6 cm × 1.5 mm–3 mm, and purple-margined. The flowers are very small and arranged in delicate pinkish heads. The corolla is 1.5 mm–2 mm long. The stamens are 4.5 mm–6 mm long and pink. The pods are 1 cm–2 cm × 4 mm, linear and slightly constricted between the seeds.

Common names: Sensitive mimosa, sensitive plant; putri malu (Malay); herbe chaste (French); mat co (Vietnamese); preah khlop (Cambodian).

Uses: In Malaysia, a paste made Pharmaceutical interest: Mimosa from the powdered leaves of Mimosa pudica L. inhibits the growth of pudica L. is used externally to soothe Gram negative Vibrio cholerae culswollen parts and a decoction of the tured in vitro (Akinsinde KA et al., plant is drunk to purify the blood. In the 1995), hence confirming the antidiarPhilippines, the roots are used to prorheal property of the plant. The antifermote urination and stop dysentery, and tility property of Mimosa pudica L. is a decoction of the plant is drunk to treat asthma. In Vietnam, a decoction of the confirmed as a root powder given intraleaves is drunk to invigorate. In Camgastrically at a dose of 150 mg/Kg body bodia, the whole herb is used to expel alters the oestrous cycle of female vesical stones, and it is applied exteralbino rats (Valsala S et al., 2002). One nally to treat oedema and rheumatism, could set the hypothesis that the invigassuage myalgia and to remove tumor orating property of the plant might be of the uterus. In India, the roots are explained by effects on both glycaemia used to stop dysentery, inhibit fertility, and depression. An ethanolic extract soothe inflammation, purify the blood, of the leaves given per os at a dose treat jaundice, leprosy, smallpox and of 250 mg/Kg, elevates significantly the asthma, and to heal ulcers. glycaemia in mice (Amalraj T et al., 2002). An aqueous extract injected intraperitonneally in rats at doses ranging from 2 mg/Kg to 8 mg/Kg, displays a significant antidepressant action similar to the antidepressant action of the drugs desipramine and clomipramine (Molina M et al., 1999). A decoction of the plant is anticonvulsant. Aqueous

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and alcoholic extracts of the dried roots of Mimosa pudica L. protect rodents against the toxic enzymes of Naja kaouthia venom (Mahanta M et al., 2001). One might set the hypothesis that the antivenom property could have resulted from the inhibition of venom metalloproteinases by mimosine (see p. 350). References Akinsinde KA, et al. (1995) J Diarrhoeal Dis Res 13(2): 127–129. Amalraj T, et al. (2002) Fitoter 73(4): 351–352. Bum EN, et al. (2004) Fitoter 75(3–4): 309–314. Mahanta M, et al. (2001) J Ethnopharmacol 75(1): 55–60. Molina M, et al. (1999) Phytomedicine 6(5): 319–323. Valsala S, et al. (2002) Phytother Res 16(2): 190–192.

Warning: Mimosa pudica L. is commonly responsible for acute and chronic livestock poisoning because of mimosine (see Leucaena leucocephala (Lamk.) de Wit). The plant is toxic. Parkia speciosa Hassk [From Latin, speciosus = beautiful] Physical description: It is a tall rainforest tree found in Malaysia, Indonesia, and Thailand. The bark is smooth and reddish-brown. Leaves: bipinnate and 15 cm–30 cm long, pinnae 10–18 pairs, swollen at the base and finely hairy, folioles 20–35 pairs, sessile, linear lanceolate, and very 5 mm–6 mm × 2 mm–3 mm. The blade is acuminate at the apex, and the base is round and asymmetric. The flowers are pollinated by bats. The fruits are stout, green, glossy, fleshy, 30 cm–50 cm × 2 cm–4 cm, leathery, pods containing several pungent seeds which are about 1 cm long and packed each in a white membrane. Common name: Stink bean, locust bean; petai (Malay); peteh (Indonesian); sato (Thai).

Pharmaceutical interest: Dietetic properties: The seeds of Parkia speciosa Hassk contain several antibacterial cyclic polysulphides which are responsible for the pungent flavor (Gmelin et al., 1981). The plant is known to contain thiazolidine-4-carboxylic acid, which protects the liver against toxic agents. It is also antiageing and an effective nitrite-trapping agent that

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inhibits the formation of carcinogenic Uses: In Indonesia and Malaysia, the N-nitroso compounds (Susilo et al., seeds of Parkia speciosa Hassk. are 1982). Stigmast-4-en-3-one charactereaten raw to treat diabetes and liver ized from a chloroform extract of the discomfort, and to expel intestinal empty pods lowers glucose levels in worms. The seeds cause smelly alloxan-induced diabetic rats confirmurination when ingested. ing thereby the antidiabetes property of the plant (Jamaluddin F et al., 1995).The exact pharmacological mechanism of action of stigmast-4-en-3-one remains unknown, but a glucocorticoid-like mechanism is possible. Note that stigmast-4-en-3-one probably has hypercholesterolaemic properties as well.

S N O Stigmast-4-en-3-one

COOH

NO Thiazolidine-4-carboxylic acid

References Gmelin R, et al. (1981) Phytochem 20(11): 2521–2523. Jamaluddin F, et al. (1995) Food Chemistry 54: 9–13. Susilo R, et al. (1982) Z Naturforsch 37c: 584–586.

Warning: Caution must be taken as the toxic effects of this plant are unknown.

2. Family CAESALPINIACEAE R. Brown in Flinders 1814 nom. conserv., the Caesalpinia Family Physical description: The family Caesalpiniaceae consists of about 150 genera and 2200 species of trees, shrubs and herbs, often producing anthraquinone glycosides and tannins. This family is the oldest family in the Fabales and is thought to have originated from the family Mimosaceae. The leaves of Caesalpiniaceae are pinnate, bipinnate or less frequently simple, and stipulate. The flowers are conspicuous, racemose, and zygomorphic.The calyx consists of 5 sepals which are imbricate and free. The

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corolla consists of 5 petals, the adaxial petal overlapped by a pair of lateral petals. The andrecium consists of 10 stamens, the anthers of which are tetrasporangiate, dithecal, and open lengthwise or by a terminal or basal pore. The gynecium is curved and consists of a single carpel, forming a unilocular ovary containing 2 to several ovules attached on a marginal placenta.The fruits are pods. Pharmaceutical interest: Classical examples of Caesalpiniaceae are Erythrophloeum guineense G. Don (sassy bark), Hymenaea courbaril L. (locust) and Copaifera pubiflora Benth. (purple heart wood). The pods of Cassia senna L. (Alexandrian senna) and Cassia angustifolia Vahl (Tinnevelly senna) have been used from time immemorial to relieve the bowels of costiveness on account of laxative anthraquinone glycosides. Tamarindus indica L. (tamarind) has been used for the same purpose but on account of organic acids. Caroub flour, obtained from the seeds of Ceratonia siliqua L., is an effective absorbent to stop diarrhea in infants. The seeds of Trigonella foenum graecum L. (fenugreek) are of dietetic value as the galactomannans they abound with lower glycaemia, cholesterolaemia and lipidaemia. Of relatively recent interest is cesalin characterized from Caesalpinia gilliesi which has been scheduled for use in pharmacology as a chemotherapeutic agent. Medicinal Caesalpiniaceae often owe their properties to laxative anthraquinones glycosides, tannins which are astringent, and saponins. H OH HO HO

HO H H

OH H

O

O

OH

COOH HOOC

OH

O

O

H HO

H H OH OH

OH HO H

Sennoside A: a laxative anthraquinones glycoside from Cassia senna L.

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Bauhinia purpurea L. [After Gaspard and Jean Bauhin, 16th century Swiss physicians and botanist and from Greek, porphura = shellfish yielding purple] Physical description: It is a deciduSynonymy: Bauhinia castrata Blanco. ous treelet native to India. The plant is ornamental and grown as such in the Common names: Butterfly tree; kupu kupu (Malay); mahahlegani Asia-Pacific. Leaves: simple and stip(Burmese); kalavilaichi (Tamil). ulate. The blade is shaped like a butterfly, coriaceous, and 7 cm–10 cm and shows 9–11 pairs of secondary nerves. The flowers are showy, purplish and arranged in axillary or terminal racemes. The fruits are darkish pods which are 1.5 cm × 15 cm and woody. Pharmaceutical interest: Tannins are Uses: In India, the roots of Bauhinia most probably responsible for the purpurea L. are used to stop medicinal properties mentioned above. flatulence. The bark is used to stop Note that daily administration of diarrhea and heal ulcers. The flowers Bauhinia purpurea L. bark extract are eaten to relieve the bowels of (2.5 mg/Kg) for 20 days stimulates thycostiveness and the bark or the roots roid function in female mice (Panda S and flowers are mixed with rice water et al., 1999). Lectins are reported and used to heal boils and abscesses. In Malaysia, the leaves (Yamamoto K et al., 1988). are used to relieve the bowels of Bauhinia purpurea L. will be worth costiveness. A paste made from the investigating as the roots of Bauhinia powdered leaves is used to heal boils malabarica contain racemosol, preraand soothe inflammation. In Vietnam, cemosol A and preracemosol B, which the roots are used to treat fever. moderately inhibit the proliferation of Plasmodium falciparum cultured in vitro. Racemosol inhibits the growth of KB and BC cells cultured in vitro with IC50 of 15 µg/mL and 6.1 µg/mL respectively (Prasat P et al., 2000).

OCH3

HO

HO

O

HO

OH OH

Racemosol Preracemosol B

O

HO

HO OH Preracemosol A

OH

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References Panda S, et al. (1999) J Ethnopharmacol 67(2): 233–239. Prasat P, et al. (2000) Phytochem 55: 349–352. Yamamoto K, et al. (1988) FEBS Lett 281(1–2): 258–262.

Warning: Caution must be taken as the toxic effects of this plant are unknown. Caesalpinia bonduc (L.) Roxb. [After A Caesalpini, 1519–1603, an Italian physician and a botanist and from Persian, finduk ] Synonymy: Caesalpinia crista L., Caesalpinia bonducella (L.) Flem. Common names: Nicker tree; gorek (Malay); yeux de bourique (French); putikaranja ´ (Sanskrit); akitmakit (Arabic).

Physical description: It is a scandent, prickly, woody and tropical climber which grows to a length of 10 m. The stems are lenticelled. Leaves: bipinnate and 1 m long. The rachis is prickly and shows several pairs of folioles which are elliptic-oblong, 2 cm–5 cm long, and obtuse or acute. The flowers are yellow and 1 cm long, arranged in axillary racemes. The fruits are 5 cm– 10 cm, inflated, and prickly pods, each containing 1–2 subglobose and leadcolored seeds (Fig. 157).

Uses: In Indonesia, the roots of Caesalpinia bonduc (L.) Roxb. are chewed to stop diarrhea and the seeds are used to expel intestinal worms. In Malaysia, a poultice of the powdered leaves is applied to the abdomen to expel intestinal worms. In the Philippines, the powdered seeds are used to treat fever, invigorate health, promote digestion and relieve the bowels of costiveness. The seeds of Caesalpinia bonduc (L.) Roxb. were known as Ibn Sina and were later named Frutex Globulorum by Georgius Everhardus Rumphius (1628–1702). In 1868, the seeds were made official in the Indian Pharmacopoeia, and were used to invigorate health and to treat malarial fever. Clinical experiments conducted in 1886 (Jour de Phar et de Chim., Aout ˆ 1886) showed that 10–20 centigrams of seeds were as effective as quinine salt in treating malarial fever.

Pharmaceutical interest: Extracts of this plant display antimicrobial, antivenom properties, as well as hypoglycaemic activity in rats (Datte JY et al., 2001; Simin K et al., 2001; Sharma SR et al., 1997; Saeed MA et al., 2001). It increases the contractile force dose-dependently in isolated portions of pregnant rat myometrium and an increase of contractile force in rat skeletal muscle via a possible role of cholinergic receptors (Datte JY et al., 1998; 2004). It will be interesting to learn whether a more intensive study on the

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Fig. 157. Caesalpinia bonduc (L.) Roxb. From: KLU 30912. Flora of Malaya. University of Malaya Herbarium. Field Collector: Omar bin Hamzah. 10 Nov 1979. Geographical Localization: Pulau Singa Besar, Pulau Langkawi. Botanical identification: AHB Loo. 27 July 1998. From: KLU Herbarium 31266. Field collector: Chia Lok Thye, 10 Nov 1979. Botanical identification: AHB Loo. 27 July 1998.

seeds of this plant will disclose any molecules of therapeutic interest. Note that the plant is known to produce bitter cassane diterpenes: caesalpinin, caesaldekanin C, F and G which are probably pharmacologically active (Peter S et al., 1998), the pharmacological potential of which remains undiscovered. OH

O

O

O

O

H H3COOC

OH

Caesaldekanin C (R= H, CH3)

H

H

H R

H H3COOC

H

H

OH

Caesaldekarin G

O

OH OAc

OAc

Caesalpinin

Caesaldekarin F (R= CH3)

References Datte JY, et al. (2001) Rev Med Pharm Afr 15: 51–57. Datte JY, et al. (1998) J Ethnopharmacol 60(2): 149–155. Datte JY, et al. (2004) Phytomedi 11(2–3): 235–241. Peter S, et al. (1998) Phytochem 47(6): 1153–1155. Saeed MA, et al. (2001) Fitoterapia 72(7): 807–809. Sharma SR, et al. (1997) J Ethnopharmacol 58(1): 39–44. Simin K, et al. (2001) Phytother Res 15(5): 437–440.

Warning: Caution must be taken as the toxic effects of this plant are unknown.

Subclass Rosidae

271

Caesalpinia sappan L. [After A Caesalpini, 1519–1603, an Italian physician and a botanist; and from Tamil, shappangam = sappan wood] Synonymy: Caesalpinia minutiflora Elmer. Common names: Sappan wood; bakkum wood; bois de sappan (French); sepang (Malay); to moc, cay vang (Vietnamese); tainniga (Burmese); sbeng (Cambodian); su fang mu (Chinese); palo de Brazil (Spanish); bakam (Arabic); pattanga (Sanskrit).

Physical description: It is a prickly treelet found in South China, Taiwan, India, Malaysia, and Vietnam. The wood is red. Leaves: bipinnate and stipulate. The pinnae are opposite and show 10–12 pairs of folioles which are 1.2 cm long and marked with about 10–15 pairs of secondary nerves. The blade is elliptic and emarginated at the apex. The flowers are arranged in terminal panicles. The corolla comprises of 5 petals which are yellow and emarginated at the apex. The andrecium comprises of 10 pubescent stamens. The fruits are coriaceous, clog-shaped, 6 cm–9 cm and caudate (Fig. 158). Pharmaceutical interest: Flavonoids: Brazilin, brazilein, protosapparin E and a mixture of sterols characterized from Caesalpinia sappan L. display an anticomplementary property (Oh SR et al., 1998). Brazilin is the principal constituent of Caesalpinia sappan L., it protects hepatocytes against BrCCl3 poisoning (Moon

Fig. 158. Caesalpinia sappan L. From: KLU Herbarium 20813. University of Malaya Herbarium. Field collector and botanical identification.: M Naskar, Apr 1975. Geographical localization: Indian Botanic Garden, Calcutta.

Uses: In China, the wood of Caesalpinia sappan L. is used to heal wounds, stop hemorrhage and haemoptysis, regulate menses after childbirth, and soothe bruises. In Malaysia, the wood is used to expel impurities and to clean infected skin. A decoction of wood is used to stop haemoptysis and hemorrhage. In Vietnam, a decoction of about 15 g of wood is ingested daily to stop dysentery, intestinal and uterine hemorrhage, heal wounds and furuncles, regulate menses, soothe contusion, and treat impetigo and leucorrhea. Externally Caesalpinia sappan L. is used as a shampoo.

272

Division MAGNOLIOPHYTA

CK et al., 1992) and the immune system of mice against halothane (Choi SY et al., 1997). Note also that brazilin inhibits the enzymatic activity of succinic semialdehyde reductase which is responsible for the degradation of GABA (Baek NI et al., 2001).The anti-inflammatory principles of Caesalpinia sappan L. are known (Hikino H et al., 1977). An extract of this plant inhibits dose-dependently the mobility of spermatozoids (Shi IM et al., 1990). In regard to the haematological properties of the plant, (6aS,cis)-Malonic acid 3-acetoxy-6a9-bis-(2-methoxycarbonylacetoxy)-6,6a,7,11b-tetrahydro-indeno[2,1-c]chromen-10-yl ester methylester has antiplatelet activities (Lee GY et al., 2005). HO

O OH H

HO

OH

Brazilin

References Baek NI, et al. (2001) Arch Pharm Res 23(4): 344–342. Choi SY, et al. (1997) Planta Med 63(5): 405–408. Hikino H, et al. (1977) Planta Med 31(3): 214–220. Lee GY, et al. (2005) Thrombosis Research 115(4): 309–318. Moon CK, et al. (1992) Drug Chem Toxicol 15(1): 81–91. Oh SR, et al. (1998) Planta Med 64(5): 456–458. Shi IM, et al. (1990) J Formos Med J Assoc 89(6): 466–469.

Warning: Caution must be taken as the toxic effects of this plant are unknown. Cassia alata L. [From Hebrew, q’ tsi’ ah = cut off bark and from Latin, alatus = having wings] Physical description: It is a handsome, prickly shrub native to tropical America which grows to a height of 2 m. The plant is invasive. Leaves: stipulate. The stipules are triangular and persistent, pinnate, and 40 cm–60 cm long. The rachis is winged and holds 4–12 pairs of folioles which are oblong, round, and slightly coriaceous. The flowers are arranged in terminal and axillary upright and showy spike-shaped racemes. The calyx comprises of 5 sepals which are

Subclass Rosidae Common names: Ringworm shrub, winged senna, ringworm senna, candelabra bush, craw craw plant, 7 golden candlesticks; gelenggang besar, daun kurap (Malay); bois puant, herbe a` dartres (French); timbo (Burmese); danghet (Cambodian); daun kurap (Javanese); acapulco (Filipino); dadrughna (Sanskrit); muong trao, cay lac (Vietnamese).

spatulate, obtuse, and 1 cm long. The corolla comprises of 5 petals which are ovate, 1.5 cm long and form a globose, golden yellow and very conspicuous corolla. The andrecium comprises of 7 stamens and 3 staminodes.The fruits are winged pods which are linear and glabrous, and contain 50–60 triangular seeds (Figs. 159 & 160).

273

Uses: Cassia alata L. is used throughout the Asia-Pacific to treat ringworm infection and to relieve the bowels of costiveness. In Malaysia, rolls of fresh leaves are rubbed on the skin to treat ringworm infection, and a paste made from the bark is used to soothe inflamed areas and shingles. In Vietnam, the leaves and stems are used to wash infected skin, relieve the bowels of costiveness, and to treat edema, herpes infection, hepatitis, and liver discomfort. The fresh leaves are used to treat ringworm infection, soothe inflammation, and treat impetigo. In the Philippines, the plant is used to treat herpes infection. In India, the leaves mixed with lime juice are used to treat ringworm infection.

Pharmaceutical interest: Antimicrobial property: Extracts of Cassia alata L. inhibit the growth of a large spectrum of bacteria and display a moderate antifungal property in vitro

Fig. 159. Cassia alata L.

Fig. 160. Cassia alata L.

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Division MAGNOLIOPHYTA

(Palanichamy S et al., 1990; Ibrahim D et al., 1995), thereby substantiating the antifungal use of this plant. Cassia alata L. contains chrysophanic acid and a number of anthraquinones glycosides which are most probably responsible for the antifungal and laxative properties of the plant. Note that a 10-year study on humans shows that an extract of the leaves of Cassia alata L. could be used to treat ptyriasis versicolor infection (Damodaran S et al., 1994). O

OH

HO

CH3 OH

O

1,5,7-Trihydroxy-3-methylanthraquinone (alatinone)

References Damodaran S, et al. (1994) J Ethnopharmacol 42(1): 19–23. Ibrahim D, et al. (1995) J Ethnopharmacol 45(3): 151–156. Palanichamy S, et al. (1990) J Ethnopharmacol 29(3): 337–340.

Warning: Caution must be taken as the toxic effects of this plant are unknown. Cassia tora L. [From Hebrew, q’ tsi’ ah = cut off bark and from Latin, torus = swelling] Physical description: It is a comCommon names: Sickle senna, mon tropical herb which grows to a sickle pod, coffee weed, foetid cassia; height of 1 m. Leaves: foetid, stipulate gelenggang kecil (Malay); petite and consisting of 6 pairs of folioles. casse puante (French); dau giau The stipules are linear and caducous. (Vietnamese); dangwe (Burmese); The folioles are obovate, apiculate, and chueh ming, tsao chueh (Chinese); 2 cm–5 cm long. A gland is present thao quyet minh, muong ngu (Vietnamese); ayudham and 10 other between the folioles of the first and names (Sanskrit). second pairs.The flowers are arranged in axillary bracteated racemes. The calyx comprises of 5 sepals which are ovate, acute and 8 mm long. The corolla comprises of 5 petals which are obovate, and 1.2 cm–1.5 cm long. The andrecium comprises of 7 stamens and 3 staminodes. The ovary is long, conspicuous, and characteristically sickle-shaped. The pods are linear, quadrangular, 15 cm × 3 mm and contain 25–30 seeds which are very small (Fig. 161).

Subclass Rosidae

Fig. 161. Cassia tora L. From: KLU Herbarium. University of Hawaii and Bishop Museum, Natural Products from the Pacific Investigations. Geographical localization: Western Samoa, village garden area. Upolu, Lefaga: Savaia. 25 m elev. Field collector: ML Bristol 1 May 1962.

275

Uses: In China, the seeds of Cassia tora L. are used to treat herpes infection, diseased eyes, and to heal infected sores. In Malaysia, the seeds are eaten to relieve the bowels of costiveness and lower blood pressure. A decoction of about 10 g of seeds is used to treat acute conjunctivis. In Vietnam and in the Philippines, the plant is used to expel intestinal worms. In Vietnam, 10 g to 15 g of raw seeds are used to relieve the bowels of costiveness, and the roasted seeds are ingested to assuage headache, relieve the bowels of costiveness, control excessive urination, treat cough, insomnia, ophthalmia and ocular congestion, and to lower blood pressure. An alcoholic or vinegar maceration of the seeds is applied externally to treat eczema and mycosis. In India, a decoction of the leaves is drunk to relieve the bowels of costiveness. The seeds and leaves are used to treat ringworm infection and irritated skin. The gum (panwar gum) expressed from the seeds of Cassia tora L. has been tried as an emulsifying, suspending and binding agent for pharmaceutical technology (Joshi S et al., 1964).

Pharmaceutical interest: Cassia tora L. contains a series of anthraquinones which are most probably responsible for the laxative and antiseptic properties mentioned above. Among these quinones are chrysophanol, chryso-obtusin, and aurantio-obtusin which protect Salmonella typhimurium against aflatoxin B1 -induced mutations (Choi JS et al., 1997). An extract of Cassia tora L. inhibits significantly the proliferation of both chloroquine-resistant and chloroquine-sensitive Plasmodium falciparum (El-Tahir et al., 1999). A methanolic extract of the leaves of Cassia sp. contracts the smooth muscles of guinea pig ileum and rabbit jejunum in a concentration-dependent manner, increases intestinal transit in mice dosedependently, and exhibits antinociceptive activity in mice (Chidume FC et al., 2002). What is the principle involved here? The seeds of Cassia tora L. lower the serum levels of lipid (Patil UK et al., 2004).

276

Division MAGNOLIOPHYTA OH

O

OH

CH3 O Chrysophanol

References Chidume FC, et al. (2002) J Ethnopharmacol 205–209. Choi JS, et al. (1997) Planta Med 63(1): 11–14. El-Tahir, et al. (1999) Phytother Res 13(6): 474–478. Joshi S, et al. (1964) Indian J Pharm 26, 78. Patil UK, et al. (2004) J Ethnopharmacol 90(2–3): 249–252.

Warning: Caution must be taken as the toxic effects of this plant are unknown. Tamarindus indicus L. [From Arabic, tamr-hindi = date of India and from Latin, indicus = from India] Synonymy: Tamarindus indica L. Common names: Tamarind tree; asam jawa (Malay); tamarindo de la India (Spanish); tamarinier (French); amli and 30 other names (Sanskrit); magi (Burmese).

Physical description: It is a tropical tree native to Africa. The twigs are reddish. Leaves: pinnate and stipulate. The stipules are small and caducous. The leaves show 8–16 pairs of folioles which are elliptic, dark green, dull and 3.5 mm × 1.5 cm. The flowers are arranged in axillary panicles.The calyx is obconial and 4-lobed; the lobes are lanceolate and imbricate. The corolla comprises of 5 yellow or purplish red Fig. 162. Tamarindus indicus L. petals. The stamens are monadelphous, and only 3 are fertile. The fruits are sausage-like, slightly rugose, fawncolored, elliptic, slightly falcate and 20 cm long.The seeds are glossy, squarish, brown, woody, and embedded in a pulp which is sourish brown and corrosive (Fig. 162).

Subclass Rosidae

Pharmaceutical interest: Tamarind pulp contains pectin, several sorts of organic acids (tartaric, malic, citric), monoterpenes, nicotinic acid, cinnamates and carbohydrates. An extensive literature exists on tamarind. Note however the presence of immunomodulatory polysaccharides (Sreelekha TT et al., 1993) and the presence of L-(-)-di-n-butyl malate which inhibit the proliferation of sea urchin embryo cells (Kobayashi A et al., 1996).

Uses: The pulp is used to relieve the bowels of costiveness, lower body temperature and quench thirst. The bark is astringent. In Vietnam, the heart wood is used to treat liver disorder, stimulate appetite, promote urination and relieve the bowels of costiveness. In Indonesia, an oil prepared from the pods is used to soothe sprue and irritated skin, heal wounds and boils and to cause an abortion. Tamarind jams are used in Western medicine as laxative remedies. OH

O HO

N

O

OH HO O

Malic acid

O

277

OH O

OH

Citric acid

HO O Nicotinic acid

References Kobayashi A, et al. (1996) Z-Naturforsch-C 51(3–4): 233–242. Sreelekha TT, et al. (1993) Anticancer Drug 4(2): 209–212.

Warning: Tamarind juice is corrosive. The leaves are toxic.

3. Family FABACEAE Lindley 1836 nom. conserv., the Pea or Bean Family Physical description: The family Fabaceae consists of 400 genera and 10 000 species of herbs, shrubs and trees. Fabaceae are known to contain tannins, mucilages, anthraquinones, isoflavonoids, triterpenoid saponins, cyanogen glycosides, quinolizidine, pyrrolizidine, indole and simple tetrahydroisoquinoline alkaloids. The family Fabaceae is thought to have originated from the family Caesalpiniaceae and it is the most advanced family of the order Fabales. In this family, the leaves are simple or compound, and stipulate. The flowers are zygomorphic with the adaxial petal overlapping the lateral petals. The andrecium comprises of 10 stamens. The

278

Division MAGNOLIOPHYTA

gynecium consists of a single carpel forming a single-locular ovary. The fruits are pods. NH

N

N

N

O

O

Cytisine

Sparteine

Pharmaceutical interest: Examples of useful products are Pisum sativum L. (peas), Arachis hypogaea L. (ground nuts), Glycine max (L.) Merr. (soya beans), and Indigofera tinctoria L. (indigo). A number of plants classified within the genera Cytisus, Laburnum, Lupinus and Crotalaria are toxic on account of quinolizidine alkaloids such as cytisine, sparteine and anagyrine. These alkaloids are strong agonists of nicotinic receptors, hence causing hypersalivation, burns in the mouth, vomiting, excitation, convulsion and death by respiratory arrest. One example is Laburnum anagyroides L. (golden chain tree) which is a leading cause of calls to poison control centers in Europe. Cytisus scoparius Link. (Scotch broom) contains sparteine which is used as a cardiac analeptic to treat stubborn cases of atrial fibrillation. A number of plant species from the genus Lupinus are responsible for untimely delivery in cattle on account of anagyrine, an alkaloid which contracts the uterus. Melilotus officinalis (yellow sweet clover), Psoralea argophylla (scurf pea), Dipterix odorata Willd. (Tonka bean) cause lethal hemorrhages on account of coumarins which inhibit blood clotting. Dolichos lablab (hyacinth bean), Lotus corniculatus (birdsfoot trefoil), Phaseolus lunatus (Lima bean), Trifolium repens (white clover) and Vicia owe their toxicity to cyanogen glycosides. Individuals genetically deficient in glucose-6-phosphate dehydrogenase develop severe haemolytic anemia (favism) after ingesting the beans of Vicia faba.

H3C

H N

O O

N

N CH 3 H CH3

Physostigmine (eserine)

H3C

O O

N +

CH3 CH3 CH3

Acetylcholine

Classical examples of pharmaceutical products are Physostigma venenosum Balf. (Calabar bean), Myroxylon balsamum (L.) Harms (Tolu basalm) and Glycyrrhiza glabra L. (liquorice). Physostigma venenosum Balf. contains physostigmine which is used to treat myasthenia gravis and primary glaucoma. Physostigmine is structurally close to acetylcholine and inhibits the enzymatic

Subclass Rosidae

279

activity of cholinesterase, an enzyme responsible for the catabolism of acetylcholine into choline. Hundreds of plant species from Fabaceae are medicinal in the Asia-Pacific. Abrus precatorius L. [From Arabic, Abrus = Abrus precatorius L. and from Latin, precatorius = pray] Physical description: It is a perennial tropical climbing shrub. The stems are slender. Leaves: pinnate and 5 cm– 8 cm long. The folioles are 20–40 in number, silky below, deciduous, membranaceous, rhomboid, and 2 cm– 3 cm long. The flowers are small and arranged in dense axillary racemes. The calyx is campanulate and 5-lobed. Uses: In Burma, the roots of Abrus precatorius L. are used to relieve cough and to adulterate liquorice. In China, the seeds are used to induce vomiting, relieve the bowels of costiveness, expel intestinal worms, stimulate the secretion of sweat, and promote expectoration. In Malaysia, a decoction of the leaves and roots is drunk to relieve cough. In Vietnam, a decoction of about 10 g of the roots, stems and leaves is drunk to treat fever, coryza and jaundice, relieve cough, and counteract poisoning. The seeds are used to treat infected skin, mastitis and galactophoritis, heal boils and soothe inflammation. A number of Asian women living in UK use the seeds to abort a pregnancy, even though these seeds are poisonous. Note that the seeds of Abrus precatorius L. were officially used in Western medicine (Abrus, British Pharmaceutical Codex, 1934).

Common names: Wild liquorice, Jamaica wild liquorice, Indian liquorice, jequirity bean, jumble beads, crab-eyes vine, coral pea, prayer beads, rosary pea; arbre a` chapelet (French); pokok memanjat, akar saga betina, akar belimbing (Malay); cam thao day, day chi chi (Vietnamese).

Fig. 163. Abrus precatorius L. From: KLU Herbarium 8633. Flora of the Caroline Islands. College of Guam Herbarium. Geographical localization: off road near teacher housing, Dinay, Southeast Yap. Climbing in trees of forest, 27 July 1966, ca 20 m. Field collectors: MW Cushing & FR Fosbery.

280

Division MAGNOLIOPHYTA

The corolla is reddish or whitish, and much exerted. The standard is ovate, acute and adheres below the staminal tube. The wings are narrow and the keel arcuate. The andrecium consists of 9 stamens which are united into a tube. The style is short and the stigma capitate. The pods are ellipsoid, 2.5 cm–4 cm long and contain 4–6 seeds. The seeds are round, glossy, woody, black and red and dreadfully toxic (Fig. 163). Pharmaceutical interest: Anti-inflammatory property: The anti-inflammatory property of Abrus precatorius L. is attributed to a number isoflavaquinones., such as abruquinone A which inhibits the aggregation of platelets, inflammation and allergy (Kuo SC et al., 1995; Wang JP et al., 1995; 1997). Other anti-inflammatory principles are triterpenes saponins (Anam EM et al., 2001). Antiviral: An aqueous extract of the seeds inhibited HIV-1 reverse-transcriptase in vitro (IC50 = 60 µg/mL; El-Mekkawy S et al., 1995). H3CO H3CO

O

O O

OCH3 OCH3

Abruquinone A

References Anam EM, et al. (2001) Phytomed 8(1): 24–27. El-Mekkawy S, et al. (1995) Chem Pharm Bull 43(4): 641–648. Hart M, et al. (1963) New Engl J Med 268, 885. Kuo SC, et al. (1995) Planta Med 61(4): 307–312. Wang JP, et al. (1995) European Journal of Pharmacology 273: 73–81. Wang JP, et al. (1997) European Journal of Pharmacology 319: 131–136.

Warning: The seeds of Abrus precatorius L. contain abrin, a glycoprotein (phytoxin), which causes, if ingested, hemorrhage, inflammation, necrosis of the liver and kidneys, stomachache, diarrhea, coma, and agglutination of red blood cells, circulatory collapse and death (Hart M et al., 1963). Alysicarpus vaginalis (L.) DC. [From Greek, halusis = chain and karpos = fruit and from Latin, vagina = sheath] Physical description: It is an upright or ascending, densely hirsute tropical herb which grows to a height of 1.5 m in vacant plots of land. Leaves: simple

Subclass Rosidae

281

Synonymy: Hedysarum nummularifolius L., Alysicarpus nummularifolius (L.) DC.). Common names: Akar seleguri (Malay).

Uses: In Malaysia, a decoction of 10 g of Alysicarpus vaginalis (L.) DC. is drunk to relieve cough, treat mumps, stimulate appetite and protect against encephalitis. In Taiwan, a decoction of Alysicarpus vaginalis (L.) DC. is used to promote digestion. Not much is known about the therapeutic potential of Alysicarpus vaginalis (L.) DC. One might set the hypothesis that the uses mentioned above are attributed to tannins.

and stipulate. The blade is hairy, elliptic, broad, retuse, lanceolate or round, Fig. 164. Alysicarpus vaginalis (L.) DC. and 1.5 cm–5 cm long.The stipules are scarious, striated and lanceolate.The flowers are 6 mm long, white, and loosely arranged in 10 cm–15 cm long and terminal racemes.The calyx is scarious and the sepals are deeply cleft. The corolla is white, the standard is broad, and the keels obtuse. The stamens are diadelphous and the anthers are uniform. The pods are cylindrical, 1.5 cm–2 cm long, rugose, puberulous and articulate in 5 indehiscent single-seeded parts (Fig. 164). Warning: Caution must be taken as the toxic effects of this plant are unknown. Erythrina subumbrans (Hassk.) Merr. [From Greek, eruthros = red] Physical description: It is a tree grown Synonymy: Erythrina lithosperma in Burma, Malaysia and the Philippines. Miq. The crown is upright. Leaves: trifoliate and Common names: Coral bean. stipulate. The folioles are as long as they are broad, each with a pair of glands at the base. The flowers are conspicuous, scarlet with whitish stripes, 2.5 cm–5 cm long and arranged in racemes. The standard is large, and the wings and the

282

Division MAGNOLIOPHYTA

keel are short.The andrecium consists of 10 stamens which project beyond the keel. A single stamen is free and the other are united into a tube where 5 long stamens alternate with 4 short ones. The pods are 8 cm–16 cm × 1.5 cm, more or less constricted between seeds, with the lower half empty and seedless, while the upper half contain 2–3 seeds. Pharmaceutical interest: The pharmacological potential of Erythrina subumbrans (Hassk.) Merr. remains unexplored til today, and will be worth studying as the Erythrina species are known to produce flavonoids and alkaloids of pharmacological interest.

Uses: In Indonesia, Erythrina subumbrans (Hassk.) Merr. is used as a post-partum remedy to check bleeding, soothe inflammation and assuage bowel discomfort. In Malaysia, the bark is used to relieve cough and stop vomiting.

Pterocarpan flavonoids: Erycristagallin from Erythrina mildbraedii inhibits carrageenan and phospholipase A2 -induced mouse paw oedema, ear oedema and inhibits chronic inflammation through the inhibition of arachidonic acid metabolism via 5-lipoxygenase pathway (Njamen D et al., 2003). Phaseollidin from Erythrina burana displays cytotoxic properties (Dagne E et al., 1993). Another cytotoxic flavonoid is wighteone from Erythrina indica which inhibits the growth of KB cells cultured in vitro with an IC50 value of 0.78 µg/mL. Isoquinoline alkaloids: Most Erythrina species contain tetracyclic isoquinoline alkaloids which paralyze the motor nerves. One such alkaloid is β-erythroidine, which has been used to anaesthetize (Dripps et al., 1947). HO

O

HO

O

O

O N

O

OH OH

O

OH

H3CO

β - erythroidine

Erycristagallin

Wighteone

References Dagne E, et al. (1993) J Nat Prod 50(10): 1831–1834. Dripps, et al. (1947) Abstr World Surg 2, 322. Njamen D, et al. (2003) European Journal of Pharmacology 468(1): 67–74. Nkengfack AE, et al. (2001) Phytochem 58(7): 1113–1120.

Warning: Caution must be taken as the toxic effects of this plant are unknown.

Subclass Rosidae

283

Indigofera tinctoria L. [From Greek, indikon = Indian dye; from Latin, ferre = bear; tinctura = dyeing]

Synonymy: Indigofera glandulifera Hayata

Physical description: It is a tropical Common names: Dyer’s indigo; shrub which grows to a height of 50 cm. indigotier tinctorial (French); nila The stems are silvery and hairy. Leaves: (Sanskrit). pinnate, 2.5 cm–5 cm, and stipulate. The folioles are 9–13 in number, obovate-oblong, 1.5 cm long and dry black. The inflorescences are axillary racemes which are nearly sessile and shorter than the leaves. The flowers are reddish-yellow and 4 mm–5 mm long. The calyx is campanulate and 5-lobed. The corolla comprises of an ovate to obovate standard and a straight keel spurred at the base. The pods are straight, 2.5 mm long and contain 8–10 seeds. The dyeing principle of Indigofera Uses: Since ancient times, Indigofera tinctoria L. is indirubin. This natutinctoria L. has been used as a dye ral product has been described as called indigo or Vitrurius Indicum by “useful in the treatment of chronic Pliny. The process of preparing indigo myelocytic leukaemia” (Han R, 1994). was first reported in the 13th century Indigofera tinctoria L. protects rats by Marco Polo, but the plant itself was against D-galactosamine and carbon unknown to Europe until the close of the 16th century. In China, Indigofera tetrachloride liver poisoning confirmtinctoria L. is used to assuage liver ing the hepatoprotective effect of the discomfort and to stop dysentery. In plant (Sreepriya M et al., 2001). Malaysia, a paste of the plant is used Note that Swiss albino mice are proto heal boils, and treat yaws and fever. tected against Dalton’s ascitic lymIn the Philippines, a decoction of the phoma by an intraperitonneal injection roots is drunk to expel stones from the of 400 mg/Kg of an ethanolic extract of kidneys. In Vietnam, the plant is used Indigofera aspalathoides. The leaves to soothe inflammation and contusion; of Indigofera oblongifolia contain a the roots are used to promote urinanumber of antimicrobial and antifuntion; and the plant is used to check gal peptides (Daho MU et al., 1999). hemorrhage. Indigofera spicata (creeping indigo) contains indospicine which is a teratogen non-protein amino acid. An aqueous extract of the fruits of Indigofera suffruticosa Mill. destroys the liver of Balbc mice and increases the number of cells with aberrant chromosome (Ribeiro CR et al., 1991). H N

O

N H O Indirubin

284

Division MAGNOLIOPHYTA

References Christina AJ, et al. (2003) Fitoterapia 74(3): 280–283. Daho MU, et al. (1999) J Ethnopharmacol 64(3): 277–282. Han R, (1994) Stem Cells Dayt 12(1): 53–63. Ribeiro CR, et al. (1991) Mem Insst Oswaldo Cruz 86 Suppl. 2. Sreepriya M, et al. (2001) Indian J Physiol Pharmacol 45(4): 428–434.

Warning: Indigofera tinctoria L. is most probably toxic. Pongamia pinnata (L.) Merr. [From Malabar, pongam = Pongamia pinnata and from Latin, pinnatus = feathered] Physical description: It is a coastal Synonymy: Cytisus pinnatus L., tree which grows in the geographiPongamia glabra Vent. cal zone spanning Malaysia to PolyCommon names: Karanja (Sanskrit); nesia. Leaves: pinnate and stipulate. mempari (Malay). The folioles are 5–7, opposite, thinly coriaceous, oblong-ovate and 6 cm– 10 cm × 3 cm–5 cm. The flowers are arranged in axillary racemes. The calyx is campanulate. The corolla is light purple and much exerted, the standard is broad, the keel obtuse, and the petals are cohering at the tip. The stamens are monadelphous, the upper filament free below. The anthers are oblong and versatile. The ovary is subsessile and contains 2 to several ovules. The style is incurved and the stigma capitate. The pods are woody, flattened, oblong, indehiscent, and 6 cm×2.5 cm–3 cm.The seeds are oily (Fig. 165).

Fig. 165. Pongamia pinnata (L.) Merr.

Subclass Rosidae

285

Pharmaceutical interest: An extract Uses: The oil expressed from the of the root given intraperitonneally seeds (pongam oil) of Pongamia to rodents displays anti-inflammatory pinnata (L.) Merr. is used externally to and analgesic properties at 50 mg/Kg treat rheumatism and infection. In (Singh RK et al., 1997). The oil India, the roots are used to soothe inflammation and counteract expressed from the seeds inhibits the putrefaction. A bath of the leaves is growth of a large number of pathogenic taken to soothe inflamed areas. bacteria at 500 µg/mL (Baswa M et al., 2001). An ethanolic extract of Pongamia pinnata (L.) Merr. destroys the Plasmodium species cultured in vitro (Simonsen HT et al., 2001). Note that the plant is known to elaborate a series of furanoflavonoid glycosides (Ahmad G et al., 2004). References Ahmad G, et al. (2004) Phytochem 65(7): 921–924. Baswa M, et al. (2001) Microbios 105(412): 183–189. Simonsen HT, et al. (2001) J Ethnopharmacol 74(2): 195–204. Singh RK, et al. (1997) Indian J Exp Biol 35(8): 831–836.

Warning: Pongamia pinnata (L.) Merr. is toxic. C. Order PROTEALES Lindley 1833 The Order Proteales consists of about 125 species of tanniferous shrubs and trees in 2 families: Proteaceae and Elaeagnaceae. Proteales are thought to have originated from the order Rosales (Appendix I).

1. Family ELAEAGNACEAE A. L. de Jussieu 1789 nom. conserv., the Oleaster Family Physical description: The family Elaeagnaceae consists of 3 genera and about 50 species of tanniferous shrubs so far known to produce ellagic acid, quebrachitol, saponins and indole alkaloids. The leaves of Elaeagnaceae are simple, alternate or opposite and without stipules. The blade and the stems are covered with starry hairs or scales. The flowers are perfect, 4-merous, strongly perigynous, and apetalous. The sepals and stamens develop from a hypanthium.The anthers are tetrasporangiate, dithecal and open by longitudinal slits. The gynecium consists of a single carpel forming a 1-locular ovary containing a solitary ovule. The fruit is succulent and often rich in ascorbic acid. Pharmaceutical interest: An example of Elaeagnaceae is Elaeagnus angustifolia L. (Russian olive) which is planted for ornamental purposes in several temperate regions. Another example is Elaeagnus multiflora, the fruits of which

286

Division MAGNOLIOPHYTA

are used to make alcoholic beverages in Japan. To date, the pharmacological potential of the family Elaeagnaceae remains mostly unexplored. In the AsiaPacific, Elaeaegnus pungens Thunb. (Elaeagnus simonii Carr.), Elaeagnus latifolia L., Elaeagnus philippensis Perr. and Hippophae rhamnoides L. are medicinal. Elaeagnus latifolia L. [From Greek, elaion = oil, agnos = name of tree and from Latin, latus = broad and folium = leaf] Common names: Mingu (Burmese); kulari (Tamil). Uses: In India and Burma, the fruits and the flowers of Elaeagnus latifolia L. are astringent. In India, the flowers are used to treat heart diseases. It will be interesting to learn whether a more intensive study on Elaeagnus latifolia L. will disclose will any molecules of therapeutic interest.

Physical description: It is a shrub found in the hilly parts of India, Ceylon, Malaysia, Indonesia, the Philippines and China. The stems are covered with starry scales. Leaves: simple, spiral and without stipules. The petiole is 6 mm–8 mm long, channeled, Fig. 166. Elaeagnus latifolia L. From: KLU and scaly. The blade is thinly cori- Herbarium 27592. Plants of Ceylon. Field aceous, elliptic, scaly beneath and collector and botanical identification: Gerrit 2.9 cm–5.5 cm × 3.5 cm–1.5 cm. The Davidse and AHM Jayasuriya. Geographical midrib is sunken above and filled Localization: Central Province. Kandy District, ca. 9 mi Northeast of Hunnasgiriya, near mile with scales. The inflorescences are post 29/21, on the road to Mahiyangana. Seccymose, short and scaly. The flowers ondary mountain forest along the road. are straw-colored and comprise of a 8 mm long scaly hypanthium from which 5 sepals which are ovate, acute and 3 mm long develop. The style is slender and scaly. The fruits are 1.4 cm × 1 cm–2.5 cm, ellipsoid, 8-ribbed with persistent lobes at the apex. The mesocarp is palatable and the seeds are 2 cm long (Fig. 166). Warning: Caution must be taken as the toxic effects of this plant are unknown.

Subclass Rosidae

287

D. Order MYRTALES Lindley 1833 The order Myrtales consists of 12 families and more than 9000 species of tropical trees, shrubs, climbers and herbs thought to have originated from the order Rosales (Appendix I). About threefourths of the species belong to the family Melastomataceae (4000) and to the family Myrtaceae (3000). The medicinal properties of Myrtales are often attributed to tannins or essential oils. Tannins are astringent, antioxidant, cytotoxic, antimicrobial but may cause neoplasia. Essential oils of several plants species classified within the family Myrtaceae are of therapeutic value: Eucalyptus globulus Labill. and Eugenia aromatica O. Ktze. (cloves).

1. Family LYTHRACEAE Jaume St.-Hilaire 1805 nom. conserv., the Loosestrife Family Physical description: The family Lythraceae consists of about 24 genera and 500 species of herbs, shrubs and trees which abound with tannins, piperidine and quinolizidine alkaloids and quinones (anthraquinones and naphthoquinones). The leaves of Lythraceae are simple, opposite and without stipules. The flowers are often 4-, 6- or 8-merous, regular, actinomorphic, strongly perigynous, and have a prominent hypanthium. The sepals are valvate and united into a tube.The petals are free, crumpled in buds, alternate with the sepals and pinnately veined. The stamens are twice as numerous as the petals and organized into 2 whorls.The gynecium consists of 2–6 carpels forming a compound, superior and plurilocular ovary. The ovules are attached to axillary placentas. A nectary disc is present. The fruits are capsular, dehiscent, and contain several oily seeds. Pharmaceutical interest: A classical example of Lythraceae is Lawsonia inermis L. (Henna, British Pharmaceutical Codex 1934) the dried leaves of which have been used to counteract putrefaction and to dye the skin and the hair since a remote period in time. O OH

O Lawsone

288

Division MAGNOLIOPHYTA

The dyeing principle of Lawsonia inermis L. is a naphthoquinones: lawsone. Other examples of Lythraceae are Lagerstroemia indica L. (crape-myrtle) and Lythrum salicaria L. (purple loosestrife), cultivated for decorative purposes. In Mexico, the leaves of Heimia salicifolia are fermented to make a beverage (sinicuichi ) which causes euphoria and hallucination. About 10 species of the plants classified within the family Lythraceae are used for medicinal purposes in the Asia-Pacific mainly on account of their astringent properties. Ammannia baccifera L. [After Paul Ammann, a 17th century German botanist and from Latin, baccifer = berry-bearing] Physical description: It is a multibranched annual herb found in the Asian paddy fields. The stems are often 4-angled. Leaves: opposite, simple, and membranaceous. The blade is oblanceolate to linear, 5 mm–5 cm × 1 mm–1 cm, narrowed at both ends and entire. The flowers are few, and arranged in dense axillary panicles. The calyx is 1 mm–2 mm long, and apetalous.The andrecium consists of 4 stamens with subglobose anthers. The fruits are globose, capsular and 1 mm– 1.5 mm long. Warning: Ammannia baccifera L. is toxic.

Synonymy: Ammannia indica Lam., Ammannia baccifera subsp. baccifera (L.) Koehne, Ammannia discolor Nakai, Ammannia vesicatoria Roxb. Common names: Blistering ammannia; kuranti (Sanskrit); kallarivi (Tamil). Uses: In the Philippines, the fresh leaves are bruised and applied to the skin to raise blisters and treat biliousness. In India, the leaves are used to stimulate appetite, relieve the bowels of costiveness, promote digestion, and stimulate venereal desire (Ayurveda). The pharmacological potential of this plant remains unexplored. Note that naphthoquinones might be responsible for the blistering properties described above.

Lagerstroemia subcostata Koehne [After M Lagerstroem, 1671–1759, a Swedish patron of science, and from Latin, sub = under and costatus = ribbed] Physical description: It is a tree Synonymy: Lagerstroemia which grows to a height of 10 m in subcostata Koehne var. haitella the lowland rainforests of Taiwan and Koehne, Murtughas subcostata Ktze., central China. Leaves: simple, subLagerstroemia unguiculosa Koehne. sessile, subopposite and membranaceous. The blade is oblong to obovate, 1.5 cm–4.8 cm × 1 cm–2.5 cm, ribbed

Subclass Rosidae

289

and acuminate and shows 3–10 pairs of secondary nerves. The flowers are arranged in conspicuous, terminal and hirsute panicles. The calyx is 5-lobed, the corolla comprises of 6 petals which are white, and 2 mm–6 mm long. The andrecium comprises of about 20 stamens. The fruits are 6 mm–8 mm long capsules opening longitudinally into 3–6 valves and containing several winged seeds. Pharmaceutical interest: The pharmaUses: In Taiwan, Lagerstroemia cological potential of Lagerstroemia subsubcostata Koehne is used to costata Koehne remains unexplored. It invigorate health and to treat fever. will be worth investigating whether a petroleum ether extract of seeds of Lagerstroemia speciosa (L.) Pers. inhibits the proliferation of bacteria in vitro (Sinhabadu A et al., 1994). The plant is known to contain ellagic acid which may be involved in the former property (Takahashi M et al., 1977). Antidiabetes property: Note that Lagerstroemia speciosa (L.) Pers. is known to produce ellagitannins: lagerstroemin, flosin B and reginin A, which increase the glucose uptake of rat adipocytes, and a triterpene corosolic acid which promotes the glucose transport activator by Ehrlich ascites tumor cells (Murakami C et al., 1993). The antidiabetic activity of an extract from the leaves of Lagerstroemia speciosa (L.) Pers. standardized to 1% corosolic acid (GlucosolR ) is confirmed in a randomized clinical trial involving non-insulin-dependent diabetes mellitus (Judy VW et al., 2003).

COOH

HO

HO Corosolic acid

References Hayashi T, et al. (2002) Planta Med 68(2): 173–175. Judi VJ, et al. (2003) J Ethnopharmacol 87: 115–117. Murakami C, et al. (1993) Chem Pharm Bull (Tokyo) 41(12): 2129–2131. Sinhabadu A, et al. (1994) Hidustan Antibiot Bull 36(1–2): 39–45. Takahashi M, et al. (1977) Yakugaku Zasshi 1977 Aug 97(8): 880–882.

Warning: Caution must be taken as the toxic effects of this plant are unknown.

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Division MAGNOLIOPHYTA

Woodfordia fruticosa (L.) Kurz Synonymy: Woodfordia floribunda Salisb., Lythrum fructicosum L. Common names: Parvati (Sanskrit); velakkai (Tamil).

Physical description: It is a shrub which grows to a height of to 2 m. It is native to Southeast Asia. The stems are terete and peeling. Leaves: simple, opposite, sessile and without stipules. The blade is lanceolate, thinly coriaceous, and 6.7 cm × 2.2 cm–5.5 cm × 1.4 cm. The midrib is sunken above and raised below. The blade shows 6– 12 pairs of secondary nerves and the base of the blade is amplexicaul. The inflorescences are axillary cymes. The flowers are tubular, red and 2.5 cm– 4 cm long. The calyx is 1.6 cm long, striated, covered with glandular dots and forming a bright red tube. The petals are longer than the sepals. The fruits are dehiscent capsules containing cuneate-ovoid, brown and small seeds (Fig. 167).

Uses: Woodfordia fruticosa (L.) Kurz is used for its astringent property. In Burma, the flowers of Woodfordia fruticosa (L.) Kurz are used to stop dysentery and colic. In Indonesia, Woodfordia fruticosa (L.) Kurz is used to stop dysentery, heal wounds, promote urination, treat sprue, and to remove blood from urine. In Malaysia, the flowers of Woodfordia fruticosa (L.) Kurz are used to promote fertility and treat smallpox. In India, the plant is used to calm uterus contractions, expel intestinal worms, to quench thirst, assuage toothache, stop dysentery, heal hemorrhoids and counteract snake poisoning.

Pharmaceutical interest: An interesting feature of Woodfordia fruticosa (L.) Kurz is that it produces a series of cytotoxic hydrolysable tannins known as woodfordins (Yoshida T et al., 1990). One such compound is wood- Fig. 167. Woodfordia fruticosa (L.) Kurz. fordin C (woodfructicosin), a dimeric From: KLU Herbarium 27553. Plants of Ceylon. Geographical Localization: UVA Province, hydrolysable tannin isolated from the Badulla District: Rawanaella waterfall, ca. leaves (Kadota S et al., 1990) which 2 miles Southeast of Ella, at mile post 13, roadinhibits the enzymatic activity of topoi- side, altitude: 750 m. 25 Nov 1974. Field collecsomerase II more potently than adri- tors: Gerrit Davidse, DB Sumithraarachchi. amycin and etoposide, alleviates the survival of PC-1 cells cultured in vitro and protects rodents inoculated with colon 38 cells (Kuramochi-Motegi A et al., 1992).

Subclass Rosidae

291

OH HO

O C

HO

O C

HO

OH O

OH O OH

O

C O

O O OC

HO

OH

OH O

HO

O OH

HO OH

HO

C O O

HO

HO OH

CO

O O O

CO O OC

HO

O

O C

OH

OH

OH HO

HO

OH OH

Woodfordin C

References Kadota S, et al. (1990) Chem Pharm Bull 38(10): 2687–2697. Kuramochi-Motegi A, et al. (1992) Biochem Pharmacol 44(10): 1961–1965. Yoshida T, et al. (1990) Chem Pharm Bull 38(5): 1210–1211.

Warning: Caution must be taken as the toxic effects of this plant are unknown.

2. Family ONAGRACEAE A.L. de Jussieu 1798 nom conserv., the Evening Primrose Family Physical description: The family Onagraceae consists of 17 genera and 675 species of tanniferous herbs abounding with ellagic and gallic acid. The leaves are simple, opposite or alternate and without stipules. The flowers are hermaphrodite, actinomorphic, and often solitary. The calyx is adnate to the ovary, and 4–5-lobed and valvate.The corolla consists of 2–5, free petals which are contorted or imbricate. The andrecium comprises of as many stamens as, or twice as many as, the calyx lobes, and the anthers are 2-locular, and open lengthwise. The gynecium is inferior and 2–6 locular and contains 1 to several ovules attached to axile placentas. The fruits are capsules, berries or nuts containing numerous seeds. COOH

HO

OH OH

Gallic acid

292

Division MAGNOLIOPHYTA

COOH Pharmaceutical potential: A number H3C of plants classified within the genγ -Linolenic acid era Fushia and Clarkia are cultivated for ornamental purposes. The fixed oil obtained from the seeds of Oenothera COOH CH3 biennis or evening primrose oil is widely marketed as a dietary suppleArachidonic acid ment for cosmetic purposes, and more specifically for the treatment of atopic O eczema and premenstrual syndrome. COOH Evening primrose has attracted a CH3 HO great deal of interest on account of OH Prostaglandin E2 its effects on diabetic neuropathy and rheumatoid arthritis. The pharmacological properties of evening primrose oil could be on account of γ -linolenic acid which is metabolized in arachidonic acid, an immediate precursor of some prostaglandins (Fig. 168). Gallic acid and ellagic acid released from hydrolysable tannins are cyto- Fig. 168. Pharmacological basis of evening toxic and are often responsible for the primrose oil: γ -linolenic acid is metabolized in antitumoral property of medicinal Ona- arachidonic acid, an immediate precursor of graceae and Rosidae in general. One prostaglandins which regulate uterus (U) contraction and inflammatory process (I). such plant is Epilobium angustifolium L., which has been traditionally used in Eurasia, which inhibits the growth of prostatic epithelial cell line (PZ-HPV-7) cultured in vitro. Epilobium tanguticum Hausskn., Epilobium angustifolium L., Ludwigia adscendens (L.) Hara, Ludwigia hyssopifolia (D. Don) Exell. Ludwigia octovalvis (Jacq.) Raven, Ludwigia prostrata Roxb., and Circaea alpina L. are mildly astringent and used in the Asia-Pacific to check bleeding, heal wounds and boils, resolve swelling, stop dysentery, expel intestinal worms, counteract fungal infection, and to treat sprue and syphilis.

Ludwigia hyssopifolia (D. Don) Exell [From Greek, hyssopos ¯ = hyssop and from Latin, folium = leaf] Physical description: It is a multiSynonymy: Jussiaea linifolia Vahl, branched and succulent herb which Jussiaea tenella Burm. f. grows to a height of 40 cm in Southeast Asia and Papua New Guinea. The stems are glabrous and somewhat angular. Leaves: simple, spiral, sessile and without stipules. The blade is lanceolate,

Subclass Rosidae Uses: In Indonesia, Ludwigia hyssopifolia (D. Don) Exell is used to maturate pimples. In Laos, Cambodia, and Vietnam, Ludwigia hyssopifolia (D. Don) Exell is used to stop diarrhea and dysentry, and to treat enteritis and sprue. In Malaysia, the roots are used to treat syphilis. It will be interesting to learn whether a more intensive study on Connaraceae will disclose any molecules of therapeutic interest.

293

Fig. 169. Ludwigia hyssopifolia (D. Don) Exell.

membranaceous, 4.5 cm × 1.5 cm–2.8 cm × 6 mm, and the nervations are inconspicuous. The flowers are axillary, solitary, and characteristically longnecked, vertical and 7 mm–2 cm long. The calyx is 4-lobed and the corolla consists of 4 deciduous petals. The fruits are linear capsules containing numerous very small seeds. The calyx lobes are persistent at the apex of the capsules (Fig. 169). Warning: Caution must be taken as the toxic effects of this plant are unknown.

3. Family MELASTOMATACEAE A. L. de Jussieu 1789, nom conserv., the Melastoma Family Physical description: The family Melastomataceae is a vast group of 200 genera and about 4000 species of tropical herbs, shrubs and trees.The leaves in Melastomataceae are simple, opposite or verticillate and without stipules. In a field collection, Melastomataceae are easily recognizable by the blade which is marked with 3–9 longitudinal and parallel nerves. The flowers are hermaphrodite, often showy, and actinomorphic. The calyx is tubular, and the sepals are free or adnate to the ovary sometimes by septa-like connections.The calyx lobes are imbricate or rarely valvate.The petals are imbricate, free, rarely united at the base, and a corona is usually present between the petals and the stamens. The stamens are as numerous or twice as numerous as the petals, and showy. The filaments are free, characteristically geniculate and inflexed.

294

Division MAGNOLIOPHYTA

The anthers are 2-locular, basifixed, and open by a single pore. The connectives are often appendaged. The ovary is inferior, 2–many locular and contains numerous ovules attached to axil placentas. The fruits are capsular or baccate and the seeds are very small. HO

HO

OH

OH HO

HO

O

OH

O

O OH O

O

O

O

OH

O

O OH O OH

H HO OH

OH

OH

OH HO

Castalagin Pharmaceutical interest: The leaves of Miconia willdenowii contain about 0.2% of caffeine and are used in Brazil to make tea. Several Asian ethnic groups use the fruits of the Melastoma species to blacken the teeth as a sign of sexual maturity, hence the word Melastoma. About thirty species of the plants classified within the family Melastomataceae are used for medicinal purposes in the Asia-Pacific. These are mostly astringent and used to stop diarrhea, check hemorrhages, heal and resolve infected or wounded skin, and for postpartum invigoration. It will be interesting to learn whether a more intensive study on Melastomataceae will disclose any molecules of therapeutic interest, especially tannins such as castalagin. Melastoma candidum D. Don [From Greek, melas = black and stoma = mouth and from Latin, candidus = white] Physical description: It is a common bush found in Asia. The stems are terete and hairy. Leaves: simple, opposite and

Common name: Senduduk puteh (Malay).

Subclass Rosidae

295

without stipules. The petiole is hairy, channeled and 7 mm–1.8 cm long.The blade is broadly lanceolate, hairy, coriaceous, 9.5 cm × 5.5 cm–7 cm × 4 cm and marked with 7 longitudinal nerves. The margin is recurved and wavy, and the tertiary nerves are conspicuous below.The inflorescences are terminal and the flowers white. The fruits are hairy and 1.2 cm × 8 mm (Fig. 170). Pharmaceutical interest: The medicinal properties of Melastoma candidum D. Don are attributed to tannins and flavonoids. Castalagin, procyanidin Fig. 170. Melastoma candidum D. Don. B-2 and helichryoide, characterized from the leaves of Melastoma canUses: In Laos, Cambodia and didum D. Don, lower blood pressure Vietnam, Melastoma candidum D. dose-dependently through a decrease Don is used to stop diarrhea, of sympathetic tone in spontaneously dysentry and leucorrhea. In Taiwan, a hypertensive rats (Cheng JT et al., decoction of the stem and leaves of 1993). Quercitrin, isoquercitrin, rutin, Melastoma candidum D. Don is drunk and quercetin, isolated from the leaves to treat fever and rickets. of Melastoma candidum D. Don, display free radical scavenging activity and inhibit MAO-B. with IC50 values of 19.06, 11.64, 3.89, and 10.89 µM respectively (Lee MH et al., 2001). OH OH HO

O

OH OH OH

OH HO

O

OH OH

Procyanidin B - 2

References Cheng T, et al. (1993) Planta Med 59(5): 405–407. Lee MH, et al. (2001) J Agr Food Chem 49(11): 5551–5555.

Warning: Caution must be taken as the toxic effects of this plant are unknown.

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Division MAGNOLIOPHYTA

Memecylon edule Roxb. [From Greek, memecylon = the fruit of Arbutus unedo and from Latin, edule = edible] Common name: Nipis kulit (Malay).

Physical description: It is a handsome coastal shrub found in Southeast Asia. The stems are terete and glabrous. Leaves: simple, opposite and without stipules. The petiole is grooved, 1 cm–1.5 cm long. The blade is elliptic-lanceolate, coriaceous, and 7.3 cm × 4.2 cm–8.6 cm × 5 cm. The midrib is sunken above and raised below. The inflorescences are axillary racemes. The fruits are pinkish, globose, open at the apex, 5 mm–7 mm in diameter (Fig. 171). Pharmacological potential:The pharmacological potential of Memecylon edule Roxb. remains unexplored. Oral administration of an alcoholic extract of Memecylon umbellatum lowers the serum glucose level in glucose and alloxan-induced diabetic mice (Amalraj T et al., 1998) on probable account of ellagic acid derivatives, flavonoids or tannins.

Fig. 171. Memecylon edule Roxb. From: KLU Herbarium 17138. Flora of Malaya. 19 Aug 1972. Geographical localization: Kedah, P. Langkawi, Pulau Timun, East end, head of rocky limestone beach, altitude: 10 ft. Field collector and botanical identification.: BCS Stone.

Uses: In Burma, the leaves of Memecylon edule Roxb. are used for their astringent properties. In Laos, Cambodia and Vietnam, Memecylon edule Roxb. is used to treat fever. In the Philippines, a variety of Memecylon edule Roxb. is used to promote menses and treat ophthalmia.

Reference Amalraj T, et al. (1998) J Ethnopharmacol 62(3): 247–250.

Warning: Caution must be taken as the toxic effects of this plant are unknown. Phyllagathis rotundifolia (Jack.) Bl. [From Greek, phylla = leaf, agathis = a ball of thread and from Latin, rotundus = circular] Physical description: It is a creeping herb found in the shady and wet spots of the Malaysian rainforest. The stems are woody. Leaves: simple,

Subclass Rosidae

297

Uses: In Malaysia, Phyllagathis rotundifolia (Jack.) Bl. is used to invigorate health after childbirth, assuage stomachache, and treat malaria and fever. The pharmacological potential of Phyllagathis rotundifolia (Jack.) Bl. and of the plants classified within the genus Phyllagathis remains unexplored til today.

spiral and without stipules.The blade is elliptic-circular, 6.9 cm × 5 cm–6.7 cm × 6.5 cm, characteristically darkish blue, somewhat fluorescent glossy on Fig. 172. Phyllagathis rotundifolia (Jack.) Bl. the surface, glaucous and velvety on the underneath. The base of the blade is cordate. The midrib and 6 parallel nerves are raised below and sunken above, and the tertiary nerves are raised below.The inflorescences are terminal racemes of about 1.5 cm long.The fruits are capsular, 4-angled, open at the apex and are 4 mm × 5 mm (Fig. 172). Warning: Caution must be taken as the toxic effects of this plant are unknown. Sonerila begoniaefolia Ridl. [From Latin, begoniaefolia = Begonialike leaves] Physical description: It is a herb which grows to a height of 50 cm in the shady and wet spots of the Malaysian rainforest.The stems are quadrangular. Leaves: simple, alternate and without stipules. The petiole is reddish. The blade is asymmetrical, 4 cm × 2 cm–9 cm × 6 cm, glossy above and marked by 4 secondary nerves parallel to the midrib which is sunken above and raised below. The inflorescences are terminal. The fruits are 1 cm×8 mm triangular capsules (Fig. 173).

Uses: In Malaysia, Sonerila begoniaefolia Ridl. is used to aid recovery from childbirth. It will be interesting to learn whether a more intensive study on Sonerila begoniaefolia Ridl. will disclose any molecules of therapeutic interest.

Fig. 173. Sonerila begoniaefolia Ridl.

Warning: Caution must be taken as the toxic effects of this plant are unknown.

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Division MAGNOLIOPHYTA

4. Family COMBRETACEAE R. Brown 1810 nom. conserv., the Indian Almond Family Physical description: The family Combretaceae consists of 20 genera and about 400 species of tropical trees and shrubs known to produce gums and tannins. The leaves are simple, without stipules, opposite, alternate or verticillate. The inflorescences are terminal and axillary racemes, spikes or a heads. The flowers are often small, unisexual or bisexual, and epigynous. The calyx comprises of 4–8 sepals, often appearing as valvate lobes on the hypanthium. The corolla comprises of up to 5 small, imbricate or valvate petals. The andrecium consists of 4–18 filaments inflexed in the buds, with versatile, tetrasporangiate and dithecal anthers opening by long longitudinal slits.The nectary disc is epigynous. The gynecium consists of 2–5 united carpels forming a 1-locular and inferior ovary containing 2–6 ovules, suspended from the apex of the ovary by slender funicles. The style is simple, and ends in a punctuate or seldom capitate stigma. The fruits are often winged and indehiscent, and contain pendulous seeds without endosperm. Pharmaceutical interest: Examples of plants classified within the family Combretaceae are Quisqualis indica L. (Rangoon creeper) and Terminalia cattapa L. (Indian almond) which are medicinal and commonly grown to decorate gardens. Terminalia chebula Retz. (myrobalan) is used as a commercial source of tannins in India. Other examples are Anogeissus latifolia Wall. (gum ghatti ), Combretum butyrosum, Terminalia bellirica Roxb. (bahera tree), Terminalia tomentosa W. & A. (asan wood), and Terminalia angustifolia Jacq. (bois benzoin). About 30 Combretaceae plant species are medicinal in the Asia-Pacific, mainly on account of their astringent properties. Quisqualis indica L. [From Latin, quis = who and qualis = what kind and indica = from India] Physical description: It is a common ornamental climber native to Burma. Leaves: the petiole is 7.5 mm long. The blade is 7.5 cm–10 cm × 3.8 cm, elliptic, acuminate, and shows 6–8 pairs of secondary nerves. The blade is round, dark green, glabrous above and hairy beneath. The inflorescences are axillary or terminal spikes. The flowers are numerous, hanging down, 7.5 cm× 4 cm, initially white, then ripening into red. The calyx is tubular, pubescent, and develops 5 triangular lobes. The

Synonymy: Quisqualis sinensis Lindl., Quisqualis indica L. var. pubescens (Burm.) Mak. Common names: Rangoon jasmine, Rangoon creeper, Burma creeper, Chinese honeysuckle, drunken sailor; dawchprincipalg (Burmese); shih chan tzu, shui chun tzu (Chinese); akar pontianak, akar suloh, belimbing hutan (Malay); liane vermifuge (French); irangunmalli (Tamil); su quan, qua gium, day gium, qua nac (Vietnamese).

Subclass Rosidae

299

petals are elliptic lanceolate, acute, and 1.3 cm long. The fruits are ellipsoid, acutely 5-angled, glabrous, and brown and 3.2 cm long (Fig. 174). O

NH2

HO

O

OH

OH

NH2

HO

N N

O

O Quisqualic acid

O

Glutamic Acid

Pharmaceutical interest: Quisqualis indica L. contains quisqualic acid: a non-protein amino acid which is ascaricidal and competes with glutamic acid to the metabotropic glutamate receptors, hence causing excitatory activity (Hansen JJ et al., 1990). Quisqualic acid may be responsible for the anticoccidal property displayed in an extract of Quisqualis indica L. (Youn HJ et al., 2001). References Hansen JJ, et al. (1990) Med Res Rev 10(1): 55–94. Youn HJ, et al. (2001) Vet Parasitol 96(4): 257–263.

Warning: Quisqualis indica L. is toxic.

Fig. 174. Quisqualis indica L.

Uses: Quisqualis indica L. is principally known for its astringent and anthelmintic properties. In Indonesia, a decoction of the fruit is drunk to expel intestinal worms. In Malaysia, the fruits are eaten to expel intestinal worms, and a decoction of the fruit is given to children to stop diarrhea. The juice expressed from the leaves is used to heal boils and ulcers, and to treat ringworm infection and fever. The roots are used to relieve cough and hiccups. In the Philippines, the plant is used to treat diseases of the chest. In Vietnam, the fruit is used to expel intestinal worms and the roots are used to soothe rheumatism and assuage gastric discomfort.

Terminalia chebula Retz. [From Latin, terminus = end] Physical description: It is a tree which grows to a height of 30 m. It is found in India, Vietnam, Burma and Thailand. The bark is dark brown, 6 mm thick and the wood is very thick. The leaf-buds, twigs and young leaves are rusty hairy. Leaves: the petiole is 2 cm–5 cm long, pubescent

Common names: Myrobalan, chebulic myrobalan; pangah (Burmese); he lip (Chinese); srama (Cambodian); mirabolanos (Portuguese); abhaya, jaya (Sanskrit); amagola (Tamil); hara, hirala (Indian); chieu lieu, kha li lac (Vietnamese).

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with usually 2 glands near the top. The blade is 7 cm–20 cm × 4 cm– 8 cm, glabrous when mature, elliptic, oblong, and shows 6–8 pairs of secondary nerves. The apex of the blade is acute, and the base is round or cordate. The inflorescences are terminal or axillary spikes. The flowers are hermaphrodite, 4 mm long, sessile, dull white or yellow and with a pungent odour. The calyx is campanulate, 3 mm long, flat at the base and 5lobed. The fruits are pendulous, 2 cm– 4 cm, almond-shaped, green, smooth, glabrous, and 5-ribbed drupes. The seeds are oblong (Fig. 175). Fig. 175. Terminalia chebula Retz.

Pharmaceutical interest: The fruits contain about 20% to 40% of tannins, Uses: The dried immature fruits of gallic acid, chebulic acid, β-sitosterol, Terminalia chebula Retz. anthraquinones and oils. Tannins and (Myrobalans, British Pharmaceutical anthraquinones make the drug both Codex, 1934) are astringent and astringent and laxative. The mature contain 20% to 40% of tannins. In fruits are used to tan in India (100000 Burma, the fruits are eaten to relieve metric tons produced in 1981). Galthe bowels of costiveness and to lic acid displays cytotoxic (Pettit GR invigorate health. In China, the fruits et al., 1996) and hepatoprotective are used to stop flatulence and promote expectoration. In India, the properties (Anand KK et al., 1997). fruits are eaten to invigorate health, Gallic and chebulic acids are immunopromote digestion and expectoration, suppressive on CTL-mediated cytosoothe sore throat and inflamed toxicity and inhibit the killing propareas, stop dysentery and vomiting, + erty of CD8 CTL clone at IC50 = and to treat ascite (Ayurveda). In 30 µM and IC50 = 50 µM respecIndonesia, the fruits are astringent. In tively, and the granule exocytose in Malaysia, the fruits are used to check response to anti-CD3 (Hamada S bleeding, assuage liver discomfort et al., 1997). Tannins extracted from and stop dysentry. In Vietnam, the Terminalia chebula Retz. do not cause fruits are used to relieve the bowels of mutations in Salmonella thyphimirium costiveness. (Kaur S et al., 1998). Tannins of the plant are antioxidant and radioprotector (Naik GH et al., 2004). Antimicrobial properties: Extracts of Terminalia chebula Retz. inhibit the growth of fungi and bacteria cultured in vitro (Ahmad I et al., 1998; Dutta BK et al., 1998). Gallic acid inhibits the proliferation of a methicillin-resistant strain of

Subclass Rosidae

301

Staphylococcus aureus (Sato Y et al., 1997). An extract of Terminalia chebula Retz. inhibits the replication of several sorts of viruses including the human cytomegalovirus (Yakawa TA et al., 1996; Shiraki K et al., 1998), the human immunodeficiency virus-1 (IC50 = 50 µg/mL; El-Mekkawy S et al., 1995) and the Herpes Simplex Virus type-1 (Kurokawa M et al., 1995). References Ahmad I, et al. (1998) J Ethnopharmacol 62(2): 183–193. Anand KK, et al. (1997) Pharmacol Res 36(4): 315–321. Dutta BK, et al. (1998) Mycosis 41(11–12): 535–536. El-Mekkawy S, et al. (1995) Chem Pharm Bull Tokyo 43(4): 641–648. Hamada S, et al. (1997) Biol Pharm Bull 20(9): 1017–1019. Kaur S, et al. (1998) Mutat Res 419(1–3): 169–179. Kurokawa M, et al. (1995) Antiviral Res 27(1–2): 19–37. Naik GH, et al. (2004) Phytomed 11(6): 530–538. Pettit GR, et al. (1996) J Ethnopharmacol 53(2): 57–63. Shiraki K, et al. (1998) Nippon Raisho 56(1): 156–160. Sato Y, et al. (1997) Biol Pharm Bull 20(4): 401–404. Yakawa TA, et al. (1996) Antiviral Res 32(2): 63–70.

Warning: Caution must be taken as the toxic effects of this plant are unknown. D. Order CORNALES Lindley 1833 The order Cornales consists of 4 families and 150 species of plants thought to have originated from the order Rosales (Appendix I) and are known to produce iridoids, tannins, alkaloids, ellagic acid, proanthocyanins and triterpenoid saponins. The family Cornaceae with about 100 species is the largest family in this order.

1. Family ALANGIACEAE A.P. de Candolle 1828 nom. conserv., the Alangium Family Physical description: The family Alangiaceae consists of the single genus Alangium which groups about 20 species of trees and shrubs containing tannins, triterpenoid saponins and isoquinoline and indole monoterpenoid alkaloids. Monoterpenoid indole alkaloids are very rare in the Rosidae and common in the Asteridae. The leaves of Alangiaceae are simple, alternate and without stipules. The flowers are perfect, arranged in axillary cymes on articulated pedicels. The calyx is truncate or 4–10-lobed. The corolla consists of 4–10 petals which are linear, valvate, and recurved. The andrecium consists of 4–40 stamens which are villous inside and free, and with 1–2-locular, linear anthers which open lengthwise. A cushion-shaped nectary disc is present.

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The gynecium consists of a pair of carpels united into a compound, 1–2-locular inferior ovary containing a single ovule which is pendulous. The style is simple, clavate or 2–3-lobed. The fruits are drupes. Pharmaceutical potential: Alangiaceae have attracted a great deal of interest on account of their ability to monoterpenoid alkaloids such as 6-O-methyl-N-deacetylipecosidic acid. Alangium chinense (Lour.) Harms, Alangium faberi Oliv., and Alangium platanifolium (Sieb. & Zucc.) Harms are medicinal in the AsiaPacific. It will be interesting to learn whether a more intensive study on the Alangiaceae will disclose any alkaloids of chemotherapeutic interest.

H3CO HO

NH H H

COOH

O H

OCLc

6 - O - methyl - N - deacetylipecosidic acid

Alangium chinense (Lour.) Harms [From Malabar, alangi chinense = from China]

=

Alangium chinense (Lour.) Harmsand from

Synonymy: Stydilum chinense Lour., Marlea begoniaefolia Roxb. Common name: Chinese Alangium; ba jiao feng (Chinese)

Physical description: It is a tree which grows to a height of 20 m. It is found in the geographical zone spanning temperate India and China. The plant is ornamental. The stems are velvety when young. Leaves: simple, alternate and without stipules. The petiole is 8 mm–1.5 cm long. The blade is asymmetrical, begonia-like, rigid, velvety below and 12 cm × 7.5 cm–7 cm × 5.5 cm. The margin is somewhat wavy. The midrib is raised on both surfaces of the blade which Fig. 176. Alangium chinense (Lour.) Harms. shows 5–7 pairs of secondary nerves and scalariform tertiary nerves. The inflorescences are axillary cymes. The calyx is very small and indistinctly lobed. The corolla consists of 8 petals which are linear, velvety and valvate (Fig. 176).

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Pharmaceutical interest: Alangium Uses: In China, Alangium chinense chinense (Lour.) Harms contains 6 (Lour.) Harms is used to invigorate O-galloyl salicilin and 4 , 6 -di-Ohealth, stop itching, assuage muscle galloylsalicilin which are probably involpains, and to treat phthisis, fever and ved in the analgesic, antipyretic and diseases of the bones and tendons. anti-inflammatory properties described In Laos, Cambodia and Vietnam, the fruits are used to treat kidney above (Itoh A et al., 2000). The myorediseases. laxant activity of Alangium chinense (Lour.) Harms is confirmed (Chang ZQ, 1981). β-Sitosterol and stigmasterol characterized from Alangium platanifolium bind to the central nervous system receptors in vitro and stigmasterol binds to the muscarinic receptors with IC50 of 8.52 µM (Min Z, 1998). Cellular properties: An alkaloid extracted from Alangium vitiense inhibits the growth of L1210 leukemia, P388 and Gardner lymphosarcoma cell-lines (Mathe G et al., 1978). A hypotensive alkaloid, choline and anthelmintic activity are reported from Alangium lamarckii (Dasgupta B, 1966; Pakrashi SC et al., 1970; Dubey MP et al., 1968). A methanolic extract of Alangium salviifolium inhibits the growth of a large spectra of Gram-positive and Gram-negative bacteria (Mosaddik MA et al., 2000). References Chang ZQ (1981) Chung Yao Tung Pao 6(5): 34–36. Dasgupta B (1966) Experientia 22(5): 287–288. Dubey MP, et al. (1968) Indian J Physiol Pharmacol 12(1): 25–31. Itoh A, et al. (2000) J Nat Prod 63(1): 95–98. Mathe G, et al. (1978) Cancer Res 38(5): 1465–1467. Min Z (1998) Planta Med 64(1): 8–11. Mosaddik MA, et al. (2000) Fitoter 71(4): 447–449. Pakrashi SC, et al. (1970) Experientia 26(9): 933–934.

Warning: Caution must be taken as the toxic effects of this plant are unknown.

2. Family CORNACEAE Dumortier 1829 nom. conserv., the Dogwood Family Physical description: The family Cornaceae consists of 11 genera and about 100 species of trees and shrubs known to contain inulin, tannins, ellagic acid, gallic acid, proanthocyanins, and iridoids. Note that iridoids are rare in the Rosidae and common in the Asteridae. The leaves in this family are opposite, alternate and mostly simple. The flowers are small, perfect or dioecious, actinomorphic, and arranged in dichotomous panicles or racemes of panicles. The calyx tube is adnate to the ovary and 4–5-lobed. The corolla comprises of 4–5 petals which are free, valvate or imbricate.The stamens are as numerous as the petals and alternate with them, and the anthers are 2-locular and open lengthwise.

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The nectary disc is cushion-shaped, central in the male flower and epigynous in female flowers. The gynecium consists of 2–5 carpels united to form a compound, inferior ovary which comprises of as many locules as carpels. Each locule encloses a single ovule. The style is simple or lobed. The fruits are drupes or berries, containing a single 1–5 locular, longitudinally grooved stone. Pharmaceutical interest: A classical example of Cornaceae is the ornamental garden shrub Cornus mas L. (Cornelian cherry wood). The barks of Cornus pubescens (dogwood) are used by the Indians in the Pacific Northwest to relieve the bowels of costiveness. Cornus florida (dogwood) has long been used by American Indians to treat fever and chills. Aralidium pinnatifidum Miq., Cornus officinalis Sieb. & Zucc., Cornus macrophylla wall., Aucuba chinensis Benth., Aucuba japonica Thunb., and Helwingia chinensis Batal. are medicinal in the Asia-Pacific. The pharmacological potential of the family Cornaceae is to date practically unknown despite the fact that the tannins of Cornus canadensis (dwarf cornel) inhibit the growth of several cancer cell-lines. It will be interesting to learn whether a more intensive study on Cornaceae will disclose any molecules of therapeutic interest. Are monoterpenoid indole or isoquinoline alkaloids present in this family? Aralidium pinnatifidum Miq. [From Latin, aralidium = aralia-like and pinnatus = feathered] Uses: In Malaysia, a paste made from the leaves of Aralidium pinnatifidum Miq. is used to produce skin irritation, treat rheumatism and fever, and heal boils. The therapeutic potential of this plant is still waiting to be discovered. By looking at the general medicinal pattern of the plant one might set the hypothesis that the plant is counter-irritant.

Common names: Balai, sebalai or selubat (Malay).

Fig. 177. Aralidium pinnatifidum Miq.

Physical description: It is a treelet found in the lowland rainforests of Thailand, Malaysia and Indonesia. Leaves: simple and deeply pinnately lobed. The petiole is 15 cm long and lenticelled, and the mature blade is 30 cm × 13 cm–80 cm × 26 cm. The inflorescences are 15 cm long panicles of several 2.5 mm long flowers. The fruits are dirty white berries which are 3.5 cm × 2.5 cm–1.5 cm×2 cm, slightly asymmetric, ovoid.The seeds are broad, elliptic, 5-grooved and deeply ruminate (Fig. 177). Warning: Caution must be taken as the toxic effects of this plant are unknown.

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305

E. Order SANTALALES Lindley 1833 The order Santalales consists of 10 families and about 2000 species of plants, some of them being parasitic and without chlorophyll, and known to produce tannins, flavonoids and various sorts of terpenes. The order Santalales is thought to have originated side by side with the Rafflesiales from the Rosales from a common ancestor. Classical examples of Santalales are Santalum album (sandalwood) and Viscum album (mistletoe).

1. Family OLACACEAE Mirbel ex A. P. de Candolle 1824 nom. conserv., the Olax Family Physical description: The family Olacaceae consists of about 30 genera and 250 species of plants which are widespread in the tropical and subtropical regions, producing tannins, cyanogenetic glycosides, acetylenic acids and flavonoids. The leaves are simple, alternate and without stipules. The flowers are small, regular, perfect, and hypogynous. The calyx is small, cupular, and lobed. The corolla consists of 3–6 petals which alternate with the calyx lobes, and are mostly valvate. The andrecium comprises of as many as and opposite the petals stamens. The gynecium comprises of 2–5 carpels united to form a compound, superior ovary, each locule containing a single ovule which is pendulous from a free and central placenta. The fruits are drupes or nuts in accrescent calyx. H3C

O S

S

S

S

CH3

O 2,4,5,7 - Tetrathiaoctane 4,4 dioxide

Physical description: An example of Olacaceae is Ximenia americana L. which is known for its valuable wood and to contain hydrocyanic acid which causes cyanide poisoning in cattle. An interesting biochemical feature of a number of plants classified within the genus Scorodocarpus, Olax, Ochanostachys and Ximenia is the presence of a series of polysulphides, such as 2,4,5,7-tetrathiaoctane 4,4-dioxide, similar to that of the Allium species (family Liliaceae, Order Liliales, Subclass Liliidae, Class Liliopsida) which are antimicrobial and cytotoxic. Olax scandens Roxb., Anacolosa griffithii Mast., Ochanostachys amentacea Mast., Scorodocarpus borneensis Becc., Strombosia philippinensis (Baill.) Rolfe and Ximenia americana L. are of medicinal value in the Asia-Pacific. To date the pharmacological potential of the family Olacaceae is virtually untouched.

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Olax scandens Roxb. [From Latin, scandere = to climb] Common names: Ailu (Burmese); mallivepam (Tamil).

Physical description: It is a tree which grows to a height of 15 m on the seashores of India, Burma, Malaysia, Vietnam, China and Indonesia. The stems are terete, smooth, and glabrous. Leaves: simple, spiral, and without stipules. The petiole is 6 mm long, channeled and rugose. The blade is rigid, 4.4 cm × 3.4 cm– 6 cm × 3.5 cm and elliptic. The midrib is sunken above and raised below. The blade shows 4–8 pairs of secondary nerves. The inflorescences are racemose and axillary. The flowers are very small, white, fragrant, and 6 mm long. The fruits are globose, 8 mm diameter drupes seated in a cupular calyx and obscurely marked at the apex by vestigial stigma (Fig. 178).

Fig. 178. Olax scandens Roxb. From: KLU 5134: Flora of Malaya. 7 Mar 1963. Geographical localization: Dungun 18 miles to Kuala Terengganu, road. In sandy area. Botanical identification:15 Jan 1970.

Uses: In Burma and India, the bark of Olax scandens Roxb. is used to combat fever.

Pharmaceutical interest: Cholinergic property : The pharmacological potential of Olax scandens Roxb. is still waiting to be discovered, but one might set the hypothesis that the antifebrile effect of Olax scandens Roxb. could be based on a choliner- Fig. 179. Hypothetive mechanism of gic mechanism since contractions of antipyretic activity of Olax scandens Roxb.: A rat fundus, antrum, and rabbit jejunum cholinergic substance (C) promotes the secreinduced by a methanol extract of Olax tion of sweat by the eccrine glands (E) which results in heat loss. gambecola are inhibited by atropine and potentiated by physostigmine (Parry O et al., 1986).

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307

Under normal physiological conditions, acetylcholine commands the secretion of sweat to the eccrine glands which results in heat loss. The antipyretic activity of Olax scandens Roxb. could therefore result from the stimulation of sweating through cholinergic stimulation of the eccrine glands (Fig. 179) just like the muscarinic agonist pilocarpine which stimulates sweat glands and was once used to remove excess water and urea in nephritis. Note the presence of choline in the closely related Loranthaceae family. This mechanism is also valid for many other antifebrile Magnoliopsida. Reference Parry O, et al. (1986) J Ethnopharmacol 18(1): 63–88.

Warning: Caution must be taken as the toxic effects of this plant are unknown. Scorodocarpus borneensis Becc. [From Greek, scorodocarpos = smelly fruit, and Latin, borneensis = from Borneo]

Physical description: It is a massive timber which grows to a height of 25 m and a girth of 2 m. It is found in the rainforests of Malaysia and Indonesia.The forested areas where this tree grows, smell of garlic. The bark is brown and scaly, and the inner bark is pinkishred, juicy and very smelly. Leaves: simple, spiral and without stipules. The petiole is 1.5 cm–1.8 cm long, curved at the apex and woody. The blade is glossy, greyish-green, rigid, obovate, and 24 cm × 9.2 cm–17 cm × 6.3 cm.

Common names: Wood garlic; pokok kulim (Malay).

Fig. 180. From: KLU Herbarium 043271. The Herbarium Waraniset, East Kalimantan, Indonesia (Flora of East Kalimantan). Field collector: Ambri, Arifin, Arbainsyah. Botanical Identificatiom: AA & Kessler. Geographical localization: Indonesia, East Kalimantan, KPC area, Bengalon, Projosamarea, Km 4, 117◦ 32 East - 00◦ 47 North, altitude: 40 m, 11 Apr 1990. Secondary forest.

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The apex of the blade is acuminate. The nervations are deeply sunken above and raised below. The blade shows 3–6 pairs of secondary nerves, and a few tertiary nerves below. The inflorescences are short axillary racemes. The flowers are greenish-white and 6 mm long.The fruits are green drupes of about 5 cm diameter, containing a single seed enclosed in a crustaceous shell. The seeds are oily and very smelly (Fig. 180). Pharmaceutical interest: Polysulphides: The garlic smell and Uses: The Malays of Perak use the the anthelminthic properties of the fresh seeds as a substitute for garlic seeds of Scorodocarpus borneenand as a medicine to remove sis Becc. are attributed to a very ringworms. In Indonesia, the seeds unusual series of polysulphides such are used to expel intestinal worms. as 2,4,5,7-tetrathiaoctane 4,4-dioxide (CH3 SCH2 SO2 SCH2 SCH3 ), 5-thioxo-2,4,6-trithiaheptane 2,2-dioxide (CH3 SO2 CH2 SCSSCH3 ), and O-ethyl S-methylthiomethyl thiosulphite (CH3 SCH2 SS(O)OCH2 CH3 which are drastically antimicrobial and cytotoxic (Lim H et al., 1998). 2,4,5-trithiahexane, 2,4,5,7-tetrathiaoctane, and 2,4,5,7-tetrathiaoctane 2,2-dioxide, and 2,4,5,7-tetrathiaoctane 4,4-dioxide inhibit rabbit platelet aggregation induced by collagen, arachidonic acid, U46619, adenosine 5 -diphosphate, platelet aggregating factor, and thrombin. This effect is on account of the inhibition of the arachidonic acid metabolism and aggregation in association with the function of the platelet plasma membrane (Lim H et al., 1999). Other substances characterized from the seeds are sesquiterpenes scodopin and cadalene-β-carboxylic acid, and a mixture of 3 tryptamine-type alkaloids, scorodocarpines A-C (Wiart C et al., 2001). O

H3C

S

S

S

S

CH3

O 2,4,5,7 - Tetrathiaoctane 4,4 - dioxide

H3C

S

S

S

O

O

CH3

O - Ethyl S - Methylthiomethyl thiosulphite

References Lim H, et al. (1998) Phytochem 48(5): 787–790. Lim H, et al. (1999) Biosc Biotechnol Biotech 63(2): 298–301. Wiart C, et al. (2001) Phytochem 58(4): 653–656.

Warning: Caution must be taken as the toxic effects of this plant are unknown.

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309

2. Family LORANTHACEAE A. L. de Jussieu 1808, nom conserv., the Mistletoe Family Physical description: The family Loranthaceae consists of about 70 genera and 700 species of tanniferous and parasitic plants known to produce phenolic acids, lignans, triterpenes, cyclitols, steroids and flavonoids glycosides (quercitrin), choline, tyramine, toxic polypeptides (viscotoxins) and glycoproteins (lectins).The leaves of Loranthaceae are simple, mostly opposite or whorled, sometimes reduced to scales, and without stipules. The blade is often characteristically somewhat spongy and glaucous, and often without distinct secondary nerves. The flowers are actinomorphic, uni-or bisexual, and often brightly colored. The calyx is adnate to the ovary, and annular or cupular. The petals are free or united into a tube, and often split down one side. The stamens are as numerous as the petals and inserted at the base of the corolla. The anthers are 2-locular. The gynecium consists of 3–4 carpels forming a compound, unilocular and inferior ovary containing 4–12 ovules attached to a free and basal central columnar placenta. The fruits are berries or drupes. Pharmaceutical interest: A common example of Loranthaceae is Viscum album L. (mistletoe) which is used as a decoration during Christmas and has long been used by Celtic shamans. The berries of this plant contain a series of toxic amines and proteins which cause gastroenteritis if eaten in large quantities. Note that a number of the plants classified within the family Loranthaceae are used to strengthen the uterus after childbirth and that Phoradendron serotinum (American mistletoe) were long used by North American Indians as oxytotic agents, namely in arresting postpartum hemorrhages. About 20 species of the plants classified within the family Loranthaceae are used for medicinal purposes in the Asia-Pacific. One may have noticed that many of these medicinal plants are used to check post-partum hemorrhages, promote the secretion of milk, soothe the pregnant uterus and to make tea-like drinks. It will be interesting to learn whether a more intensive study on the family Loranthaceae will disclose any molecules of therapeutic interest. Macrosolen cochichinensis (Lour.) van Tieghem [From Latin, cochinchinensis = from Cochinchina] Physical description: It is a Southeast Synonymy: Elytranthe Asian parasitic plant which grows on cochichinensis G. Don, Elytranthe trees. The stems are rugose, terete and globosa G.Don. glabrous. Leaves: simple, opposite and without stipules. The petiole is 3 mm– 6 mm long and flattened above. The blade is elliptic or lanceolate, thick, and shows a midrib sunken above and raised below.The inflorescences are axillary

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racemes of about 2.5 cm long. The fruits are small berries seated on persistent calyx lobes and with a funnelshaped body at the apex (Fig. 181). Uses: In Laos, Cambodia and Vietnam, the leaves of Macrosolen cochichinensis (Lour.) Van Tieghem are used to make a tea-like drink, and the fruits are used to treat cough. In Malaysia, Macrosolen cochichinensis (Lour.) Van Tieghem is used to assuage headache, and to tighten the uterus after childbirth. To date, the pharmacological potential of Macrosolen cochichinensis (Lour.) Van Tieghem is undiscovered.

Warning: Caution must be taken as the toxic effects of this plant are unknown.

Fig. 181. Macrosolen cochichinensis (Lour.) van Tieghem. From: KLU 355111. Flora of Singapore. Comm. Ex. Herb. Hort. Bot. Sing. Geographical localization: Nec Soon, open forest margins bordering the swamp, along a stream, epiphytic, hemi-parasite. Altitude: 5 m. 23 Sep 1982. Field collector & botanical identification: JF Maxwell.

Dendrophthoe pentandra (L.) Miq. [From Greek, pente = five and andro = male] Synonymy: Loranthus pentandrus L. Uses: In Laos, Cambodia and Vietnam, the leaves of Dendrophthoe pentandra (L.) Miq. are used to make a tea-like drink used to treat cough. In Malaysia, Dendrophthoe pentandra (L.) Miq. is used as a remedy to and recovery from childbirth, and to heal sores, wounds and ulcers. The pharmacological potential of this plant is yet to be discovered.

Fig. 182. Dendrophthoe pentandra (L.) Miq.

Physical description: It is a Southeast Asian parasitic plant which grows on trees. The stems are terete and glabrous. Leaves: simple, opposite and without stipules. The petiole is 1 cm × 3 cm–5 mm × 3 mm. The blade is fleshy, thick, somewhat leathery and spongy, elliptic-lanceolate, 11.7 cm × 4 mm–13 cm × 4.3 cm and exhibits a showy midrib. The inflorescences are short and axillary

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311

racemes. The calyx is cupular and 3 mm long. The corolla is tubular, 1.5 cm– 2 cm long and somewhat reddish. The petal lobes are linear, recurved downward and 5 mm–1 cm long. The stigma is showy and the andrecium comprises of 5 stamens. The fruits are red and succulent (Fig. 182). Warning: Caution must be taken as the toxic effects of this plant are unknown. F. Order RAFFLESIALES Kerner 1891 The order Rafflesiales consists of 3 little families: Hydnoraceae, Mitrastemonaceae and Rafflesiaceae, and about 60 species of fleshy, parasitic, tropical herbs without chlorophyll. The order Rafflesiales is thought to have originated side by side with the Santalales from the Rosales in which they share a common ancestor (Appendix I).

1. Family RAFFLESIACEAE Dumortier 1829 nom. conserv., the Rafflesia Family Physical description: The family Rafflesiaceae consists of about 7 genera and 50 species of very unusual parasitic plants confined to the rainforests of Asia. The leaves are whorled and without normal stomata. The flowers, the largest in the Magnoliopsida, are fleshy, smelly, showily colored, and mostly unisexual. The perianth consists of 4–5 imbricate tepals. The andrecium consists of 5 to numerous stamens connate by their filaments into a tube surrounding the stylar column, from which the anthers originate in 1 to several cycles. The gynecium consists of 4–8 carpels united into a compound, inferior or half inferior ovary crowned by a stout columnar style and containing several ovules attached to parietal placentas. The fruits are fleshy, dehiscent or not, and contain numerous small seeds. Pharmaceutical interest: A classical example of Rafflesiaceae is Rafflesia arnoldii R. Br. from Sumatra which has the largest flowers in the world (1 m across). Rafflesia hasseltii Suring., Rafflesia patma Bl., and Rhizanthes lowii (Becc.) Harms are of medicinal value. It will be interesting to learn whether a more intensive study on the family Rafflesiaceae will disclose any molecules of therapeutic interest. Rafflesiaceae are an endangered species and their chance of survival is slim. Rafflesia hasseltii Suring [After Sir Thomas Stamford Raffles, an 18th century patron of science and founder of the British colony at Singapore] Physical description: It is a fleshy parasitic herb which grows attached to the roots of trees in the rainforests of Malaysia and Indonesia. The

312

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Common name: Rafflesia. Uses: In Malaysia, the dried buds are used to expedite delivery in and aid recovery from childbirth. The pharmacological potential of this plant is unknown.

buds are spherical, darkish and open noisily at night into giant flowers of about 60 cm to 1 m diameter which are whitish and penciled in red. The perianth comprises of 5–6, 25 cm × 16 cm tepals around a hollowed receptacle at the bottom of which are displayed a few finger shaped organs (Fig. 183).

Fig. 183. Rafflesia hasseltii Suring.

Warning: Caution must be taken as the toxic effects of this plant are unknown.

G. Order CELASTRALES Wettstein 1907 The order Celastrales consists of 11 families and about 2000 species of woody plants thought to have originated from the order Rosales (Appendix I), and known to produce tannins, lignans, triterpenes, sesquiterpenes, and alkaloids, including sesquiterpene, purine, pyridine and occasionally monoterpenoid isoquinolines alkaloids. The order Celastrales is thought to have originated with the Rhamnales from the Rosales in which they share a common ancestor. Celastraceae, Hippocrateaceae, Aquifoliaceae and Icacinaceae are fairly closely related. The Dichapetalaceae stand somewhat apart from the order families and are excluded by some authors from the Celastrales and referred to as the Euphorbiales.The presence of monoterpenoid isoquinolines in the Icacinaceae suggests that Celastrales and Cornales might have common ancestry in the Rosales.

1. Family CELASTRACEAE R. Brown in Flinders 1814 nom. conserv., the Bittersweet Family Physical description: The family Celastraceae consists of about 50 genera and 800 species of trees, shrubs and climbers, which are principally tropical, and often containing phenethylamines, pyridine, and purine alkaloids, triterpenes, sesquiterpenes, lignans, and cardenolides (Euonymus). The leaves of

Subclass Rosidae

313

Celastraceae are simple, often glossy and serrate, alternate or opposite, and with or without stipules. The inflorescences are terminal or axillary cymes. The flowers are hermaphrodite, small, actinomorphic, greenish or white, hypogynous and succulent. The perianth comprises of 5 sepals and 5 petals which are small, imbricate or rarely valvate. The andrecium consists of 5 stamens which are alternate with the petals, and inserted in or below the margin of a conspicuous nectary disc. The anthers are tetrasporangiate and dithecal. The gynecium consists of 2–5 carpels forming a superior, 2–5-locular ovary. The styles are terminal, short and capitate, and develop a 2–5-lobed stigma. The fruits are capsules, samaras, berries or drupes. Cl H3CO

O N O

OR O

H3CO

HO

N H

O

Maytansine (R= COCH(CH3)N(CH3)COCH3)

Pharmaceutical interest: The leaves of Catha edulis Forsk. or khat, are used in a number of African and Arab countries to stimulate the intellect and to assuage hunger. The active principle of khat is (-) – cathinone, an epinephrine-like phenethylamine alkaloid derived from phenylalanine and tyrosine (Fig. 184). Another classical example of Celastraceae is the ornamental Euonymus europaeus L. (spindle tree), the fruits of which are poisonous. Euonymus (British Pharmaceutical Codex, 1954) consists of the dried root-bark of Euonymus atropurpureus and has been used as a tinctue (0.6 mL– 2.6 mL), a mild purgative and choleretic. To date, pharmacological studies on NH2

HO O

NH2 CH3

CH3 HO

( - ) Cathinone

OH

Noradrenaline

NH2 Amphetamine

Fig. 184. Examples of neuroactive natural products characterized from the family Celastraceae. Similitude of chemical structure of (-) – cathinone, noradrenaline and amphetamine.

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Division MAGNOLIOPHYTA

Celastraceae have provided very interesting results and the discovery of natural products of therapeutic interest is very probable in this family. A number of the plants classified within the genus Maytenus and Puterlickia contain macrocyclic alkaloids of possible bacterial origin, such as maytensine, which are able to inhibit experimentally the proliferation of tumors at very low dosage (µg/Kg of animal body weight). Triptolide and tripdiolide, diterpenes characterized from Tripterygium wilfordii display potent antileukemic properties. About 30 plant species of Celastraceae are medicinal in the Asia-Pacific. O O O

OH

O O Triptolide

Celastrus monospermoides Loes. [From Greek, kelastros = the name of another tree and from monos = alone and sperma = seed] Synonymy: Celastrus malayensis Ridl. Uses: In Malaysia, the leaves of Celastrus monospermoides Loes. are applied externally to treat fever. The pharmacological potential of Celastrus monospermoides Loes. is unexplored.

Physical description: It is a woody climber which grows in the Malaysian rainforest. The stems are glabrous, terete and smooth. Leaves: simple, spiral and without stipules. The petiole is 1 cm–1.4 cm, thin, channeled and transversely striated. The blade is glossy above, glabrous,

Fig. 185. Celastrus monospermoides Loes. From: KLU Herbarium 13486: 15 Apr 1970, E Soepadmo. Botanical identification: Ding Hou, 9/1983. Geographical localization: Hill dipterocarps. Forest along Sungai Sempam, Raub, Pahang, Malaysia.

Subclass Rosidae

315

9.5 cm×4.5 cm–10 cm×5 cm, thick, elliptic, and serrate. The apex of the blade is slightly acuminate and the base acute.The midrib is sunken above and raised below, and the secondary nerves, about 7 pairs, are indistinct above. The inflorescences are axillary, 5 cm–10 cm long racemes. The fruits are 3-lobed, dehiscent, 1.5 cm × 1 cm capsules containing a seed which is embedded in a yellowish-orange aril (Fig. 185). Warning: Caution must be taken as the toxic effects of this plant are unknown. Celastrus paniculata Willd. [From Greek, kelastros = the name of another tree and from Latin, panus = ear of millet] Synonymy: Celastrus paniculatus Willd. Common names: Black oil tree, climbing staff plant, intellect tree; myinkoungnayoung (Burmese); may thee (Cambodian); amruta (Sanskrit); adibaricham (Sanskrit); day sang mau (Vietnamese).

Physical description: It is a large and deciduous climber which grows in the geographical zone spanning India, China, Australia and New Caledonia. The stems are 20 cm in diameter and up to 18 m long. The twigs are fairly smooth reddish-brown and lenticelled. The bark is pale brown and 7.5 mm–1 cm thick.The inner bark is not fibrous. It is pink and finely streaked with red lines, which turns Fig. 186. Celastrus paniculata Willd. blue upon light exposure. Leaves: 6.3 cm–10 cm × 3.8 cm–7.5 cm, simple, spiral, without stipules. The petiole is 7.5 mm–1.5 cm long. The blade is thick, glabrous, broadly elliptic, ovate or obovate, and acuminate. The margin is crenate-serrate, and the secondary nerves arching. The flowers are 3.8 mm long, green, and arranged in terminal, deciduous, 5 cm–20 cm long panicles. The fruits are 3-lobed, bright yellow, 3– 6-seeded, 1 cm–1.3 cm globose capsules which are depressed. The seeds are enclosed in a red aril (Fig. 186).

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Division MAGNOLIOPHYTA

Pharmaceutical interest:

Uses: In Burma, the seeds of Celastrus paniculata Willd. are used to invigorate health, and the leaves are used to counteract opium poisoning. In India, the leaves are used to promote menstruation, and the seeds are used to relieve the bowels of costiveness, produce venereal desire and stimulate the intellect. In Indonesia, the leaves are used to stop dysentery. In the Philippines, the pulverized seeds are used to treat rheumatism and paralysis, and to invigorate health. In Vietnam, the oil expressed from the seeds is used to treat beriberi.

Psychoanaleptic property : The oil expressed from the seeds of Celastrus paniculata Willd. given per os (50 mg/Kg, 200 mg/Kg or 400 mg/Kg) to young adult rats for 14 days, completely reverses the scopolamine (0.5 mg/Kg)-induced impairment in a navigational memory test (Gattu M et al., 1997). The same oil tested in a 2 compartment passive memory test improved the retention ability of albino rats. This effect is accompanied with a decrease in the brain content of noradrenaline, dopamine and serotonine (Nalimi K et al., 1995). What is the active principle involved here? An alkaloid? Anti-inflammatory and analgesic properties: A methanolic extract of the flowers of Celastrus paniculata Willd. displays both analgesic and anti-inflammatory properties per os in the hot water immersion test using mice and inhibits the paw oedema induced by carrageenan in rats (Ahmad F et al., 1994). This anti-inflammatory property may involve a number of polyols or a number of flavonoids (anthocyanidins?) since both dulcitol (a hexahydric sugar alcohol) and (−)-epiafzelechin (a flavan-3-ol) characterized from Celastrus orbiculatus Thumb. are anti-inflammatory. Dulcinol improves significantly the collagencaused arthritis in mice with a T-cell modifying property (Kobayashi Y et al., 1997). (−)-Epiafzelechin inhibits dose-dependently cyclo-oxygenase with an IC50 of 15 µM and significantly reduces the paw oedema induced by carrageenan in mice at 100 mg/Kg per os (Min KR et al., 1999). Cytotoxic and antiviral properties: The plants classified within the genus Celastrus are interesting because they often contain cytotoxic and/or antiviral sesquiterpenes and triterpenes. Sesquiterpenes characterized from Celastrus stephanotrifolius inhibit the development of tumors at low doses (Takaishi Y et al., 1993). Maytenfolone A, a triterpene characterized from Celastrus hindsii, destroys efficiently HEPA-2B cells (ED50 : 2.3 µg/mL) and KB cells (ED50 : 3.8 µg/mL) cultured in vitro. B, another triterpene, celasdin B, inhibits the replication of the Human Immunodeficiency Virus in H9 lymphocytes with an EC50 of 0.8 µg/mL (Kuo YH et al., 1997). Furthermore, a number of sesquiterpenes characterized from the roots of Celastrus orbiculatus partially or completely reverse the resistance of KB-V1 and MCF7/ADR cells to adriamycin, vinblastine and taxol (Kim SE et al., 1998; 1999). It will be interesting to learn whether a

Subclass Rosidae

317

more intensive study on Celastrus paniculata Willd. will disclose any terpenes of therapeutic interest. O O

H OH O

Maytanfolone A (R=OH)

References Ahmad F, et al. (1994) J Ethnopharmacol 43(2): 193–198. Gattu M, et al. (1997) Pharmacol Biochem Behav 57(4): 793–799. Kobayashi Y, et al. (1997) Nippon Yakurig Z 110(1): 132–137. Kim SE, et al. (1998) J Nat Prod 61(1): 108–111. Kim SE, et al. (1999) J Nat Prod 62(5): 697–700. Kuo YH, et al. (1997) Phytochem 44(7): 1275–1281. Min KR, et al. (1999) Planta Med 65(5): 460–462. Nalini K, et al. (1995) J Ethnopharmacol 47(2): 101–108. Takaishi Y, et al. (1993) J Nat Prod 56(6): 815–824.

Warning: An oily extract of the seeds of Celastrus paniculata Willd. causes vacuolization, germ cell depletion and the arrest of spermatogenesis in the testis of treated rats, suggesting an antifertility effect. Euonymus alatus (Thunb.) Sieb. [From Greek, eu = good and onoma = name and from Latin, alatus = wing] Physical description: It is a shrub Synonymy: Euonymus found in China, Korea and Japan which thunbergianus Bl., Euonymus striatus is often cultivated as an ornamental var. alatus Mak. plant. The bark is greyish, and the Common name: Winged Euonymus, stems are characteristically winged. cork bush, burning bush. Leaves: simple, opposite and without stipules. The petiole is very small, glabrous and channeled. The blade is 3.5 cm × 1.3 cm, thin, orbiculate, reddish, and shortly acuminate at the apex. The margin is serrulate. The midrib

318

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is raised on both surfaces, and the secondary nerves are indistinct. The flowers are solitary or cymose and axillary on 5 mm long pedicels.The corolla comprises of 4 petals which are irregular, ovate, yellow, small and nerved. The andrecium consists of 4 stamens which alternate with the petals. The nectary disc is showy and succulent (Fig. 187). Uses: In China, the stem of Euonymus alatus (Thunb.) Sieb. is used to treat fever, expel intestinal worms, and regulate blood circulation and menses. In Korea, the stems are used to treat schizophrenia, check bleeding, lower blood pressure and assuage abdominal pain after parturition.

Fig. 187. Euonymus alatus (Thunb.) Sieb. From: KLU Herbarium 10108. Collection: 9 June 1965. Botanical identification: M Togashi. Geographical localization: Idzumino, Chinoshi, Pref. Nagano, Japan.

Pharmaceutical interest: Butanol and chloroform extracts of the stems of Euonymus alatus (Thunb.) Sieb. inhibit the growth of human hepatocellular carcinoma cell line, Hep3B cells with IC50 values of 65 µg/mL and 85 µg/mL respectively (Cha BY et al., 2003). Euonymus alatus (Thunb.) Sieb. increases the production of nitric oxide by macrophages. Note that nitric oxide is a potent derived effector molecule against tumors (Chung HS et al., 2002). Euonymus alatus (Thunb.) Sieb. lowers plasma HDL3-c level and slow down the progress of atherosclerosis (Wang W et al., 1991). It will be interesting to learn whether a more intensive study on Euonymus alatus (Thunb.) Sieb. will disclose any molecules of chemotherapeutic interest. Note that 3,4-dihydroxycinnamic acid from the plant inhibits the enzymatic activity of metalloproteinase inhibitor (Park WH et al., 2005). References Cha BY, et al. (2003) J Ethnopharmacol 85(1): 163–167. Chung HS, et al. (2002) Clinica Chimica Acta 318(1–2): 113–120. Park WH, et al. (2005) Toxicology 207(3): 383–390. Wang W, et al. (1991) Zhongguo Zhong Yao Za Zhi 16(5): 299–301.

Warning: Caution must be taken as the toxic effects of this plant are unknown.

Subclass Rosidae

319

Gymnosporia spinosa (Blco.) Merr. & Rolfe [From Greek, gumnos = naked, spora = spore and from Latin, spina = thorn] Synonymy: Catha spinosa Forsk., Gymnosporia montana (Roth.) Benth., Celastrus senegalensis Lam.). Common names: Bahuphala (Sanskrit); valuluvai (Tamil).

Physical description: It is a shrub found in Southeast Asia. The stems when young are prickly. Leaves: drying yellowish, thick, and 3 cm–5 cm × 2 cm–3.8 cm. The petiole is 3 mm– 10 cm long. The blade is elliptic or obovate, round at the apex, entire or crenulate, and tapered at the base. The inflorescences are axillary cymes. Fig. 188. Gymnosporia spinosa (Blco.) Merr. & Rolfe. The flower pedicel is long and thin, and the bracts are small and lanceolate. The calyx lobes are very small, broadly elliptic-oblong, round at the apex, and ciliate. The petals are 3 mm long and elliptic-oblong. The filaments of the stamens are flattened and dilate at the base. The nectary disc is succulent and 10-lobed. The ovary is glabrous and orbicular. The style is fertile flowers and deeply 2–3-lobed. The fruits are 5 mm long globose capsules ripening into purple. The seeds are glabrous, chestnut brown, rugose and embedded in an aril (Fig. 188). Pharmaceutical interest: Hepatoprotective property: A methanolic extract of leaves of Gymnosporia montana lowers the enzymatic activity of transaminases, the level of lipid constituents and the level of orosumucoid in the serum, and the level of glycogen in the liver of animals poisoned with carbon tetrachloride (De S et al., 1994).

Uses: In the Philippines, a decoction of the leaves of Gymnosporia spinosa (Blco.) Merr. & Rolfe is drunk to assuage headache. In India, the fruits are used to promote digestion, expel impurities, heal ulcers and piles, soothe inflammation and treat corneal opacities (Ayurveda), fever and biliousness.

Cellular property: The plants classified within the genus Gymnosporia are interesting because they contain compounds which are DNA strandscission agents such as syringaldehyde, (−)-syringaresinol, (+)-catechin, and (+)-epicatechin characterized from Gymnosporia trigyna (Deng JZ et al., 2000).

320

Division MAGNOLIOPHYTA OCH3 OH O H H3CO

H

OCH3

O

HO OCH3 Syringaresinol

References De S, et al. (1994) Planta Med 60(4): 301–304. Deng JZ, et al. (2000) J Nat Prod 63(9): 1269–1272.

Warning: Caution must be taken as the toxic effects of this plant are unknown.

2. Family HIPPOCRATEACEAE A. L. de Jussieu 1811 nom. conserv., the Hippocratea Family Physical description:The family Hippocrateaceae consists of the genera Hippocratea (100 species) and Salacia (200 species). Hippocrateaceae are tanniferous, tropical shrubs or climbers closely allied to the Celastraceae.The leaves of Hippocrateaceae are mostly opposite and simple and the stipules small or absent. The inflorescences are cymose. The flowers are small, hermaphrodite and actinomorphic. The calyx is small, and consists of 5 imbricate sepals. The corolla comprises of 5 petals which are imbricate or valvate. A cupular, conical or expanded nectary disk is present. The andrecium comprises of mostly 3 stamens which alternate with the petals. The gynecium consists of 3 carpels united to form a compound, superior, trilocular and somewhat triangular ovary containing 2–10 ovule per locule which are attached to axile placentas. The style is subulate or short and mostly 3-fid. The fruit are drupes, berries, or capsules. The seeds are compressed and often winged or angular. Pharmaceutical interest: Hippocrateaceae are interesting because they produce sesquiterpene pyridine alkaloids that will be worth assessing for their cytotoxic and other pharmacological potential. Hippocratea indica Willd., Salacia flavescens Kurz, Salacia grandiflora Kurz, Salacia macrophylla Bl. and Salacia prinoides (Willd.) DC. are medicinal in the Asia-Pacific. The roots of these plants are often used to promote menses and used to aid recovery from childbirth.

Subclass Rosidae OR6

R1O

OR5 OR4

R2O O O

321

O OH OR3 O O

N R1= Ac, R2= CNMP, R3= Ac, R4= COPh, R5= Ac, R6= Ac

Salacia grandiflora Kurz [From Latin, grandis = large and flores = flowers] Physical description: It is a climbing shrub which grows in the rainforests of Malaysia. The stems are lenticelled and glabrous. Leaves: simple, subopposite and without stipules. The petiole is channeled above and 6 mm–8 mm × 1.75 mm–2 mm long. The blade is rigid, elliptic-obovate, 18.5 cm–20.5 cm×6.7 cm–9.2 cm.The apex of the blade is apiculate and the base acute. The margin is recurved and somewhat wavy. The midrib is raised above and below. The blade shows 7–10 pairs of secondary nerves raised on both surfaces. The flowers are 2.5 mm long, pink and cauliflorous. The fruits are globose, 3.5 cm diameter berries containing several 3-lobed seeds of 2 cm length (Fig. 189). Pharmaceutical interest: To date, the pharmacological properties of Salacia grandiflora Kurz. are unknown.

Fig. 189. Salacia grandiflora Kurz. From: KLU Herbarium 19209. Flora of Malaya. Field collector & botanical identification: SC Chin. Geographical Localization: Perak, Ipoh, Gunong Rapat, Limestone 100 m.

Uses: In Malaysia, a decoction of the roots of Salacia grandiflora Kurz. is used to promote menses.

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Antidiabetes properties: Note that the Salacia species are interesting because they produce various sorts of α-glucosidase, α-amylase, sucrase, isomaltase and aldose reductase inhibitors of possible therapeutic value for the treatment of diabetes. Examples of α-glucosidase inhibitors are sulphonium salacinol and kotalanol both characterized from Salacia reticulata and Salacia oblonga, which also strongly inhibit α-amylase and sucrase respectively (Yoshikawa M et al., 1998; Matsuda H et al., 1999; Ghavami A et al., 2001). Mangiferin characterized from Salacia reticulata inhibits sucrase, isomaltase and aldose reductase with IC50 values of 87, 216, and 1.4 µg/mL (Yoshikawa M et al., 2001).The friedelane-type triterpene kotalagenin 16-acetate characterized from Salacia oblonga inhibits aldose reductase (Matsuda H et al., 1999). Other properties: Quinone methides from Salacia kraussii display in vitro antimalarial activity (Figueiredo JN et al., 1998). The root bark powder of Salacia oblonga assuages the paw edema induced by carrageenan in male albino rats (Ismail TS et al., 1997). Isoiguesterin, an antileukemic bisnortriterpene, was characterized from Salacia madagascariensis, a plant also known to have strong antimalarial properties in vitro (Gessler MC et al., 1994). HO

-O3SO

CH2OH H

S+ HO CH2OH

H OH

Salacinol

References Figueiredo JN, et al. (1998) J Nat Prod 61(6): 718–723. Gessler MC, et al. (1994) Acta Tropica 56(1): 65–77. Ghavami A, et al. (2001) J Am Chem Soc 123(26): 6268–6271. Ismail TS, et al. (1997) J Ethnopharmacol 56(2): 145–152. Matsuda H, et al. (1999) Chem Pharm Bull 47(12): 1725–1729. Sneden AT, et al. (1981) J Nat Prod 44(4): 503–507. Yoshikawa M, et al. (1998) Chem Pharm Bull 46(8): 1339–1340. Yoshikawa M, et al. (2001) Yakugaku Zasshi 121(5): 371–378.

Warning: Caution must be taken as the toxic effects of this plant are unknown.

3. Family AQUIFOLIACEAE Bartling 1830 nom. conserv., the Holly Family Physical description:The family Aquifoliaceae consists of 4 genera and about 400 species of cosmopolitan, evergreen trees and shrubs which are known to produce triterpenoid saponins, flavonoids, and purine or pyridine base alkaloids. The leaves in this family are simple, alternate, with or without stipules.

Subclass Rosidae

323

The flowers are actinomorphic and hermaphrodite or not. O CH3 The inflorescences are cymose, fasciculate or seldom soli- H C 3 N N tary. The calyx comprises of 4 sepals which are small and imbricate. The corolla consists of 4 petals which are N O N imbricate or valvate and shortly connate at the base. The CH3 andrecium comprises of 4 stamens which are alternate with the petals, free and with dithecal and tetrasporangiate Caffeine anthers opening by longitudinal slits. The gynecium consists of 4–6 carpels united to from a compound, superior ovary with as many locules as carpels, each locule containing 1 or 2 pendulous ovules. The style is terminal and short or indistinct. The fruits are berries containing as many stones as carpels, and they are poisonous. Pharmaceutical interest: Classical examples of Aquifoliaceae are Ilex aquifolium L. (common holly) and Ilex opaca Aiton, which are extensively cultivated for use as Christmas decorations. A number of the plants classified within the genus Ilex contain caffeine and are used to make invigorating beverages — America: Ilex paraguariensis (yerba de mate, mate, Paraguay tea), Ilex guayusa; North America: Ilex cassine (cassina, dahoon holly), Ilex verticillata (winter berry) and Asia: Ilex chinensis. Note that there is an expanding body of evidence to suggest that a daily intake of yerba de mate promotes aerodigestive tumors. Ilex asprella Champ., Ilex chinensis Sims, Ilex cornuta Lindl., Ilex yunnanensis Franch., Ilex godajan (Coleb. Ex Wall.) Wall. and Ilex wallichii Hook f. are of medicinal value in the Asia-Pacific. Ilex pubescens Hook. & Arn. [From Latin, ilex = Quercus ilex and from pubescere = soft down] Synonymy: Ilex trichoclada.

Physical description: It is a small and evergreen rainforest shrub found in China and Taiwan. Leaves: 4 cm– 5.5 cm × 1.5 cm–2 cm and simple. The blade is oblong or lanceolate, and the apex of the blade acute. The margin is subentire or remotely serrate. The secondary nerves are indistinct. The flowers are arranged in axillary cymes. The fruits are globose, 4 mm–5 mm berries containing 4–5 pyrenes.

Uses: In China and Taiwan, a decoction of the leaves is drunk to invigorate health, stop flatulence, lower body temperature, expel impurities, promote urination and to abort a pregnancy. A paste made from the leaves is used to treat skin diseases, counteract snake-poisoning and heal poisoned wounds. In China, the plant is used to stimulate blood circulation and treat coronary diseases.

324

Division MAGNOLIOPHYTA

Pharmaceutical potential: Generally speaking, the Ilex species owe their pharmacological potential to tannins, flavonoids, triterpenoid saponins and purine bases (caffeine and theobromine). Antioxidant/antiradical properties: Hyperoside, rutoside and chlorogenic acid characterized from Ilex aquifolium L. inhibit non-enzymatic lipid peroxydation in model membrane (Muller K et al., 1998). The intraperitonneal injection of an aqueous extract of Ilex paraguariensis inhibits dose-dependently the oxidation of low density lipoproteins (Gugliucci A et al., 1995).The same aqueous extract given to healthy humans who fasted, inhibits copper-induced autoxidation of low density lipoproteins in the whole plasma (Guggliucci A, 1996). This aqueous extract inhibits the contraction caused by methoxamine in a mesenteric arterial bed, and this effect is reversed by N-(G)-nitro-L-arginine methyl ester suggesting the involvement of nitrous oxide of endothelial reserve (MucilloBaisch AL et al., 1998). Cardiovascular properties: Ilex pubescens Hook. & Arn. is interesting because it contains a series of triterpenoid saponins such as ilexonin A, which could hold some potential for the treatment of cardiovascular diseases (Wang Z et al., 1993). Ilexonin A inhibits the aggregation of platelets and calcium influx in platelets. Thrombin significantly reduces the level of platelet cyclic adenosine monophosphate (cAMP) while ilexonin A and the calcium-channel blocker verapamil antagonize this effect. Ilexonin A inhibits platelet phosphodiesterase more potently than verapamil, which is currently used to treat angina pectoris, hypertension and arrhythmia. Other properties: Asprellic acids A and B, triterpenoids characterized from Ilex asprella, inhibit the growth of RPMI-(7951) cell-line (0.62 µg/mL and 5.5 µg/mL) and KB cells (3.75 µg/mL and 2.86 µg/mL) cultured in vitro (Kashiwada KL et al., 1993). Ilexoside XLVIII and cynarasaponin C inhibit in vitro acyl OH OH HO

O H

O OH

HO

O

O H

H

HO HO Hyperoside

H OH H

Subclass Rosidae

325

CoA cholesteryl acyl transferase, a key enzyme in the synthesis of cholesterol (Nishimura K et al., 1999). Rotundic acid, a triterpene characterized from Ilex integra, inhibits in vitro the proliferation of a broad spectrum of microbes (Haraguchi H et al., 1999). The antidepressant property of the plant has been substantiated experimentally in rodent (Xu C et al., 2004). References De Stefani E, et al. (1991) Cancer 67(2): 536–540. De Stefani E, et al. (1996) Canc Epid Biom Prev 5(7): 515–519. Guggliucci A, et al. (1995) Biochem Mol Biol Int 35(1): 47–56. Guggliucci A, et al. (1996) Biochem Biophys Res Com 224(2): 338–344. Haraguchi H, et al. (1999) Phytother Res 13(2): 151–156. Kashiwada Y, et al. (1993) J Nat Prod 56(12): 2077–2082. Leitao AC, et al. (1994) Braz J Med Biol Res 27(7): 1517–1525. Mucillo-Baisch AL, et al. (1998) J Ethnopharmacol 60(2): 133–139. Mac Gee JOD, et al. (1976) J Clin Path 29, 788. Muller K, et al. (1998) Planta Med 64(6): 536–540. Nishimura K, et al. (1999) J Nat Prod 62(8): 1128–1133. Wang Z, et al. (1993) Chin Med Sc J 8(4): 215–217. Xu C, et al. (2004) J Ethnopharmacol 91(2-3): 345–349.

Warning: Caution must be taken as the toxic effects of this plant are unknown. Note that Mate solutions, which have become popular for their antioxidant/antiradical properties, are however mutagen in the Ames test (TA97, TA98, TA100, TA102 strains, 20 mg/plates to 50 mg/plates) and genotoxic (WP2s strain; Leitao AC et al., 1994) showing that antioxidant/antiradical natural products can be noxious. Furthermore, a case-control study which includes 497 cases of lung cancer and the same number of controls, reveals that mate is associated with risks of upper aerodigestive tract cancer (De Stefani E et al., 1996). A case-control study involving interviews with 111 incident cases and 222 controls shows a high mortality rate for bladder cancer, on account of black tobacco smoking and mate ingestion (De Stefani E et al., 1991). The case of a young woman who developed a veino-occlusive disease after drinking mate over a number of years is reported by Mc Gee et al. (1976).

4. Family ICACINACEAE Miers 1851 nom. conserv., the Icacina Family Physical description: The family Icacinaceae consists of about 50 genera and 400 species of trees, shrubs and woody climbers of tropical distribution which are known to produce purine and monoterpenoid isoquinoline alkaloids, iridoids, saponins and proanthocyanins. The leaves are simple, alternate and without stipules. The flowers are hypogynous, actinomorphic, and perfect. The calyx is small, 4–5-lobed, and the lobes are imbricate or rarely valvate. The corolla is tubular or dialypetalous, and valvate. The stamens are as numerous as the petals and alternate with them. The anthers are tetrasporangiate and

326

Division MAGNOLIOPHYTA

dithecal, with free filaments which are hairy and borne on the corolla. The gynecium consists of 2–5 carpels united to form a compound, mostly singlelocular ovary, containing a pair of pendulous ovules from near the top of the ovary. The style is short. The fruits are berries. Pharmaceutical interest: A very interesting feature of Icacinaceae is the presence of monoterpenoid alkaloids, such as emetine, which are wellknown for their emetic, amebicidal, antiviral and cytotoxic properties. It will be interesting to learn whether a more intensive study on the family Icacinaceae will disclose any monoterpenoid alkaloids of chemotherapeutic interest. Gonocaryum subrostratum Pierre, Gonocaryum gracile Miq., Gonocaryum calleryanum (Baill.) Becc., Gomphandra quadrifida (Bl.) Sleum. var. angustifolia (King) Sleum., Gomphandra quadrifida (Bl.) Sleum. var. ovalifolia (Ridl.) Sleum., and Rhyticarium sp. are used for medicinal purposes in the Asia-Pacific.

H3CO N

H3CO

H H N

H H

OCH3 OCH3 Emetine

Gomphandra quadrifida (Bl.) Sleum. var. angustifolia (King) Sleum. [From Greek, gomphandros = naillike male and from Latin, quadri = four and fidere = cut] Synonymy: Gomphandra salicifolia Ridl. Uses: In Malaysia, a decoction of the leaves of Gomphandra quadrifida (Bl.) Sleum. var. angustifolia (King) Sleum. is drunk to aid recovery from childbirth. The pharmacological potential of Gomphandra quadrifida (Bl.) Sleum. var. angustifolia (King) Sleum. remains unexplored til today.

Physical description: It is a small rainforest tree found in Malaysia. Leaves: simple, alternate and without stipules. The petiole is 4 mm– 5 mm long and channeled. The blade

Fig. 190. Gomphandra quadrifida (Bl.) Sleum. var. angustifolia (King) Sleum. From: KLU Herbarium. Plants of Ulu Gombak. Geographical localization: Ulu Gombak, 16th mile, UM Field Studies Center, West Malaysia. Field collector: Benjamin C Stone, 10 Nov 1965. Botanical identification: H Sleumer/70 (RijksHerbarium. Leiden).

Subclass Rosidae

327

is elliptic-linear, rigid, 6.8 cm×1.5 cm–6.6 cm×1.6 cm.The apex of the blade is acuminate. The margin is wavy. The midrib is deeply sunken above and raised below.The blade shows 4–6 pairs of secondary nerves which are indistinct.The inflorescences are axillary and hairy cymes of 5 mm–2 cm long. The flowers are very small (Fig. 190). Warning: Caution must be taken as the toxic effects of this plant are unknown.

5. Family DICHAPETALACEAE Baillon in Martius 1886, nom. conserv., the Dichapetalum Family Physical description:The family Dichapetalaceae is a small group of 3 genera and about 235 species of shrubs and woody climbers, principally found in Africa and known to produce fluoroacetic acid and pyridine alkaloids. The largest genera of Dichapetalaceae is the genus Dichapetalum with 200 plant species. The leaves are simple, alternate, stipulate and glandular. The inflorescences are cymes. The flowers are perfect, regular, hypogynous and characteristically fluffy and 5-merous. The stamens alternate with the petals. The anthers are dithecal and open longitudinally. The gynecium consists of 2–3 carpels united into a compound 2–3-locular ovary, each locule containing a pair of apicalaxile, pendulous, and anatropous ovules. The style is simple. The fruits are berries containing a few seeds. Pharmaceutical interest: An example of Dichapetalaceae is Dichapetalum cymosum the grazing of which causes high mortality in cattle and wild animals in South Africa. The Dichapetalum species abound with cardiotoxic fluoroacetic acids which irritate the skin, provoke a tingling sensation around the corners of the mouth and numbness of the face, and cause pulmonary congestion, oedema, froth in the airways and hemorrhagic gastroenteritis. In the Asia-Pacific, Dichapetalum griffithii (Hook. f.) Engl. is medicinal. The pharmacological potential of the family Dichapetalaceae remains unexplored. Dichapetalum griffithii (Hook. f.) Engl. [From Latin, petalum = petals, and after Dr. William Griffith, a 19th century botanist and curator of the Botanic Garden in Calcutta] Physical description: It is a climber found in the rubber estates and

Synonymy: Chailletia griffithii Hook. f.

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Uses: In Malaysia, Dichapetalum griffithii (Hook. f.) Engl. is used as a post-partum remedy. The pharmacological potential of Dichapetalum griffithii (Hook. f.) Engl. is unknown. The seeds of Dichapetalum toxicarium contain long-chain fluoro-fatty acid and fluoroacetic acid, which causes death (10 mg/Kg) attributable to severe bradycardia (Tosaki A et al., 1988).

villages of Malaysia and Indonesia. The stems are lenticelled and pilose at the apex. Leaves: alternate and simple.The petiole is 2 mm × 2 mm–3 mm and pilose. The blade is rigid, pilose beneath, and 20 cm × 7 cm–15 cm × 3 cm. The midrib is flat above and raised below. The blade shows 8–10 pairs of secondary nerves. The fruits are fluffy, yellow, axillary, globose, 1.5 cm × 1.7 cm–7 mm × 6 mm and seated in a persistent calyx (Fig. 191).

Fig. 191. Dichapetalum griffithii (Hook. f.) Engl. From: KLU 00317. Flora of Malaya. Field collector & botanical identification: M. Kassim, 23 Jan 1961. Geographical Localization: altitude: 250 feet, RRI Sungei Buloh.

O F

OH

Fluoroacetic acid

Reference Tosaki A, et al. (1988) Basic Research Cardiology 83(2): 158–166.

Warning: Caution must be taken as this plant is certainly poisonous on account of fluoroacetates.

Subclass Rosidae

329

H. Order EUPHORBIALES Lindley 1833 The order Euphorbiales consists of 4 families and about 8000 species of trees, shrubs, herbs and climbers which are thought to have originated from the order Celastrales (Appendix I).

1. Family EUPHORBIACEAE A. L. de Jussieu 1789 nom. conserv., the Spurge Family Physical description: The family Euphorbiaceae consists of 300 genera and about 7500 species of trees, shrubs, herbs, climbers and even cactusshaped plants, often exuding a milky poisonous latex, and known to produce hydrolysable tannins, aporphine, pyridine, indole, and tropane types alkaloids, lignans, phloroglucinol derivatives, various sorts of terpenes, ellagitannins, proanthocyanins and, cyanogen glycosides, anthraquinones and fatty acid epoxides. The leaves of Euphorbiaceae are simple or compound, alternate and stipulate or not. Several sorts of inflorescences occur in the family. The flowers are small and unisexual. The perianth is inconspicuous to seldom showy, and comprises of 5 tepals which are distinct or connate. The andrecium consists of 5 or more stamens which are tetrasporangiate, dithecal, and open by longitudinal slits. A nectary disc is present. The gynecium consists of 3 carpels forming a compound and 3-locular ovary with 3 distinct styles, each locule containing 1–2 ovules. The fruits are characteristically dehiscent trilobed capsules. Pharmaceutical interest: A classical example of Euphorbiaceae is tapioca (Manihot esculenta Crantz), which is one of the dietary plants most anciently used by mankind. The seeds of Ricinus communis L. provide castor oil, which has been used since a remote period in time to relieve the bowels of costiveness. Rubber is prepared from the latex of Hevea brasiliensis Muell. Arg. (hevea rubber). Euphorbiaceae are often toxic. An example of toxic Euphorbiaceae is Excoecaria oppositifolia, the latex of which causes blindness and anaphylactic shock to the lumberjacks of Southeast Asia. At least 14 genera including Aleurites, Croton, Euphorbia, Hippomane, Hura and Jatropha owe their toxicity to complex diterpenoid esters of the tigliane, ingenane or daphnane type. Almost all of these compounds are drastic cathartics, causing intense contact inflammation, and are both tumor-promoting and anti-tumor agents. One such compound is 12-O-tetradecanoylphorbol-13-acetate, which is one of the most potent inducer of skin tumor in mice. As a pharmacological tool, it is valuable because it activates the phosphorylation enzyme, protein kinase C. Note that this diterpene displays interesting anti-HIV activity in vitro.

330

Division MAGNOLIOPHYTA O O

OH

H

O

OCOCH3

OH OH

12 - O - tetradecanoylphorbol - 13 - acetate

Euphorbiaceae contain proteins (phytoxins), which are among the most violent existing poisons. One such protein is curcin from Jatropha curcas, and ricin from Ricinus communis L. Being often toxic, Euphorbiaceae should be used with caution in herbal remedies. Minor drugs still used are Croton tiglium (croton oil), and Croton eleuteria Benn. (cascarilla bark). About 150 species of the plants classified within the family Euphorbiaceae are used for medicinal purposes in the Asia-Pacific. Most of these are used to relieve the bowels of costiveness, soothe inflammation, and promote urination and expectoration. It will be interesting to learn whether a more intensive study on Euphorbiaceae will disclose any molecules of therapeutic interest. Note that hydrolysable tannins and diterpenes are predominantly responsible for the medicinal properties of Euphorbiaceae. Acalypha indica L. [From Greek, a = without, kalyphos = a cover and from Latin, indica = from India] Physical description: It is a light green and smelly herb found in shady vacant plots in the tropical regions which grows to a height of 90 cm. lt is slightly hairy and branched, and its odour is adored by cats.The stems are woody at the base. Leaves: simple and alternate.The petiole is 5 cm long.The blade is broadly ovate, 3 cm × 4.5 cm, and dentate. The base of the blade is wedge-shaped, and the apex blunt. The inflorescences are 2.5 cm–10 cm

Common names: Common acalypha; cika mas, cika emas (Malay); kuppaimeni (Tamil); hierbal del cancer (Spanish).

Subclass Rosidae

331

Uses: Acalypha indica L. is principally used to relieve the bowels of costiveness and to expel intestinal worms. The fresh or dried entire flowering plant (Acalypha, British Pharmaceutical Codex, 1934) was used in Western medicine to promote expectoration and to induce vomiting, in a way similar to ipecacuanha in the form of a liquid extract (1 in 1, dose 0.3 mL to 2 mL) or a tincture (1 in 8, dose 2 mL to 4 mL). In Malaysia, a decoction of the whole plant is drunk to expel intestinal worms. A decoction of the roots is drunk to treat asthma, pneumonia and rheumatism. In the Philippines, the juice expressed from the plant is used to promote expectoration and to induce vomiting. In Vietnam, the leaves are used to expel intestinal worms and the roots to relieve the bowels of costiveness. Note that the young shoots are often used as vegetables.

Fig. 192. Acalypha indica L.

long spikes, the lower part of which shows rather large and showy, green, conical and lobed bracts, concealing the female flowers. The male flowers consist of 4 sepals and 8 free stamens packed together at the apex of the spikes.The fruits are small 3-lobed capsules hidden in the bracts (Fig. 192). Pharmaceutical interest: Acalypha indica L. elaborates a cyanogen glycoside: acalyphine, which is responsible for the smell and is possibly involved in some of the properties described above. Extracts of Acalypha indica L. display antimicrobial properties, and petroleum ether and ethanolic extracts of Acalypha indica L. (600 mg/Kg) inhibit the implantation in female albino rats (Camabadusuriy et al., 1994; Lamabadusuriya SP et al., 1994, Sellahewa K, 1994). This antifertility property is reversible upon withdrawal of the treatment of the extracts and could be of oestrogen origin (Hiremath SP et al., 1999). Of recent interest is the neutralization potential of Viper russelli russelli (Russell’s viper) venom by an ethanol extract of the leaves (Shirwaikar A et al., 2004). H OH H O

HO HO

H H

OCH3 NC O

OH H HO

N CH3

Acalyphine

O

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Division MAGNOLIOPHYTA

References Camabadusuriy, et al. (1994) Ceylon Med J 39(1): 45–46. Hiremath SP, et al. (1999) J Ethnopharmacol 67(3): 253–258. Lamabadusuriya SP, et al. (1994) Ceylon Med J 39(11): 46–47. Sellahewa K. (1994) Ceylon Med J 39(3): 145. Shirwaikar A, et al. (2004) J Ethnopharmacol 94(2–3): 267–273.

Warning: Excessive ingestion of this plant causes cyanide-like intoxication. Cases of haemolysis following the ingestion of Acalypha indica L. in G6PD deficient subjects are reported (Camabadusuriy et al., 1994; Lamabadusuriya SP et al., 1994; Sellahewa K, 1994). Acalypha siamensis Oliv. ex Gage [From Greek, a = without, kalyphos = a cover and from Latin, siamensis = from Siam] Synonymy: Acalypha evrardii Gagnep. Common name: Kernam (Malay). Uses: In Malaysia, an infusion of the leaves is used to assuage bowel and kidney discomfort, and a paste made from the leaves is applied externally to treat fever. In Vietnam, an infusion of the leaves and flowers is drunk to promote urination. The therapeutic potential of Acalypha siamensis Oliv. ex Gage is unknown.

Fig. 193. Acalypha siamensis Oliv. ex Gage.

Physical description: It is a shrub found in Malaysia, India, Indochina, Thailand and Burma which is often cultivated as an ornamental plant. Leaves: simple, spiral, and 3.7 cm × 1.5 cm. The blade is pointed, glossy, and light green. The base is wedge-shaped. The margin is dentate, and the apex is acute. The inflorescences are short spikes with the male flowers above the female flowers at the base. The flowers are apetalous and without a nectary disc. The male flowers consist of 4 sepals and 8 free stamens. The female flowers consist of

Subclass Rosidae

333

3–5 sepals, and are characteristically enclosed in 5 mm bracts. The fruits are small 3-lobed spiny capsules splitting into 3 valves (Fig. 193). Warning: Caution must be taken as the toxic effects of this plant are unknown. Acalypha wilkesiana M. A. [From Greek, a = without, kalyphos = a cover and after Admiral Charles Wilkes, 19th century American naval officer and explorer in the South Pacific] Common names: Beef steak plant, copper plant; fire dragon. Uses: In Malaysia, a beverage consisting of about 60 g of the leaves boiled in goat’s milk is drunk to lower blood pressure, treat fever, relieve cough and heal pimples. It is said that about 10 g of the leaves boiled with sugar is used to treat trombocytopenic purpurea and allergic purpurea. Fig. 194. Acalypha wilkesiana M. A.

Physical description: It is a tropical bush which grows to a height of 1.5 m. It is cultivated for ornamental purposes all over the Asia-Pacific. Leaves: simple, spiral, and reddish. The inflorescences are spikes bearing male flowers at the top and female flowers at the base. The flowers are apetalous and without a nectary disc. The male flowers consist of 4 sepals and 8 free stamens. The female flowers are enclosed in a 5 mm bract. The fruits are small 3-lobed capsules splitting into 3 valves (Fig. 194). Pharmaceutical interest: Antibacterial properties: Water and ethanolic extracts of the leaves of Acalypha wilkesiana M. A. inhibit moderately the proliferation of standard and local strains of bacteria and fungi including Staphylococcus aureus, Trichophyton rubrum, Trichophyton mentagrophytes, Candida albicans and Aspergillus flavus confirming thereby the antiseptic property of the plant.The ethanolic extract inhibits the proliferation of Klebsiella pneumoniae and Proteus mirabilis. The minimum inhibitory concentrations of these extracts range between 0.25 mg/mL and 32 mg/mL, while the minimum

334

Division MAGNOLIOPHYTA

cidal concentrations are between 1 mg/mL and 64 mg/mL.The aqueous extract is found to be static in action while the ethanolic extract is bactericidal in effect (Alade PI et al., 1993). Geraniin, gallic acid, and corilagin are the antimicrobial constituents of Acalypha wilkesiana M. A. and Acalypha hispida leaves (Adesina SK et al., 2000). Note that geraniin is also known to lower blood pressure (see Sapium sebiferum). In addition, geraniin is known to decompose into gallic acid, ellagic acid and corilagin with boiling water. Gallic acid is cytotoxic. OH HO

OH

OH

O

HO O HO O

OH HO

O H O

O

H H

OH O

O

OH H

O O

OH

O O HO OH OH

OH

Geraniin

Cytotoxic properties: Aqueous and ethanolic extracts of Acalypha wilkesiana M. A. seeds cause the apoptosis of lymphocytes and the generation of reactive oxygen intermediates. In granulocytes, the aqueous extract of the seeds induces an oxidative burst and enhances the phagocytosis of Escherichia coli. Both extracts stimulate the release of the pro-inflammatory cytokines tumor necrosis factor α and interleukin6, as well as T-cell-associated cytokines interleukin 5 and interferon γ (Bussing A et al., 1999). References Adesina SK, et al. (2000) Phytother Res 14(5): 371–374. Alade PI, et al. (1993) J Ethnopharmacol 39(3): 171–174. Bussing A, et al. (1999) J Ethnopharmacol 66(3): 301–307.

Warning: Caution must be taken as the toxic effects of this plant are unknown.

Subclass Rosidae

335

Alchornea villosa (Benth.) Muell.-Arg. [After S. Alchorne, 1727–1800, an English botanist; and from Latin, villus = shaggy hair] Physical description: It is a treelet which grows to a height of 4 m in the primary rainforests of Malaysia and Indonesia. The stems are smooth, and hairy when young. Leaves: simple, spiral and stipulate. The stipules are linear, 5 mm–7 mm long, and hairy. The petiole is hairy, constricted at the base and of 1.5 cm–9.8 cm long. The blade is hairy, lanceolate, very thin, and 18.5 cm × 11.3 cm–5 cm × 1.6 cm. The margin is serrate. The apex of the blade is acuminate in a 1 cm–3.5 cm long tail. The base exhibits a pair of small stipules of about 5 mm × 1 mm and a pair of discshaped, 0.75 mm in diameter, occasional glands. The blade shows 5–10 pairs of secondary nerves and conspicuous scalariform tertiary nerves. The inflorescences are axillary spikes of 6.5 cm–15 cm in length. The fruits are green, woody, smooth, capsular, 2lobed and develop at the apex 3 long stigma of 1.2 cm–1.5 cm (Fig. 195).

Fig. 195. Alchornea villosa (Benth.) Muell.Arg. From: KLU Herbarium 33970. Flora of Johore, West Malaysia. Comm. Ex. Herb. Hort. Bot. SING. Field collector & botanical identification: JF Maxwell. 10 April 1982. Geographical localization: Kota Tinggi Waterfalls (Air Terjun).

Pharmaceutical interest: Headaches Uses: In Indonesia, Alchornea villosa and dizziness are symptoms of hyper(Benth.) Muell.-Arg. is used to tension, and one might set the hypothassuage headache, and to treat fever esis that the plant has hypotensive and dizziness. In Malaysia, the roots properties, but this has yet to be conare used to relieve itch. firmed. In regard to the pharmaceutical potential of Alchornea species, a number of experiments conducted in vitro have demonstrated promising pharmaceutical properties. Extracts of Alchornea cordifolia inhibit the growth of a large spectrum of micro-organisms, Plasmodium falciparum, and Trypanosoma sp. cultured in vitro and relax portions of smooth muscles (Ogungbamila FO et al., 1990; Okeke IN et al., 1999; Mustofa et al., 2000; Adewunmi CO et al., 2001). Are ellagitannins such as isocorilagin or gallic acid known to occur in Alchornea triplinervia

336

Division MAGNOLIOPHYTA

(Braca A et al., 2002) involved here? Is Alchornea villosa (Benth.) Muell.-Arg. antimicrobial? HO

OH

OH

OH

HO

OH O

O O

OH O

O O OH

O OH

OH OH

Isocorilagin

References Adewunmi CO, et al. (2001) J Ethnopharmacol 77(1): 19–24. Braca A, et al. (2002) Biochemical Systematics and Ecology 30(11): 1109–1111. Mustofa, et al. (2000) J Ethnopharmacol 73(1–2): 145–151. Ogungbamila FO, et al. (1990) Acta Pharm Nord 2(6): 421–422. Okeke IN, et al. (1999) Phytoter Res 13910: 67–69.

Warning: Caution must be taken as the toxic effects of this plant are unknown. Aleurites moluccana (L.) Willd. [From Greek, Aleurites = wheaten flour and from Latin, moluccana = from the Moluccas] Physical description: It is a tree which Synonymy: Aleurites triloba Forst. grows to a height of 18 m and a girth of 50 cm. It grows in the geographic Common names: Candleberry tree; area spanning Malaysia and the Pacific aleurite des Moluques, bancoulier (French); tosikyasi (Burmese); shih Islands. When cut, the bark exudes a leih (Chinese); wai-wai (Fijian); buah clear watery sap. The stems, petioles, keras (Malay); akhota (Sanskrit); and blades are covered with a whitish nattu-akhrotu (Tamil). starry tomentum. Leaves: simple, spiral and without stipules. The petiole is 11.5 cm–15 cm and thin. The blade is lanceolate, rigid, 3–5-lobed, 7.8 cm × 4 cm–12.5 cm × 16.2 cm and marked at the base with a pair of 1 mm diameter, disc-shaped glands. The margin is recurved. The nervations are raised on both surfaces of the blade which shows 6–7 pairs of secondary nerves. The inflorescences are terminal panicles. The calyx is 2.5 mm long, 2–3-lobed and covered with a whitish starry tomentum. The corolla is 1.3 cm across,

Subclass Rosidae

Fig. 196. Aleurites moluccana (L.) Willd. From: KLU Herbarium 9541. Flora of the Society Islands, Island of Raiatea, Bernice P Bishop Museum. Field collector & botanical identification: John W Moore, 26 Sep 1926. Geographical localization: in most shady valley 1 mile south of Uturoa, altitude 300 feet. From: KLU Herbarium 5886. Flora of Malaya. Field collector & botanical identification: Benjamin C Stone. 5 Mar 1966. Geographical localization: Serdang Agric. Expt. Station, Selangor, altitude: 200 feet.

smelly and dull-white. The fruits are woody, 5 cm–6.3 cm, olive-colored capsules containing a pair of oily seeds (Fig. 196).

337

Uses: Georgius Everhardus Rumphius (1628–1702) states that the Javanese and Macassars make candles from the seeds which are either pounded and mixed with coconut, or simply strung on a piece of split bamboo. In India, where the tree was much cultivated, the seeds were known as Indian walnuts. Dr Rorke (Ann. de Therap., ´ 1859, p. 117) reported that 1 to 2 ounces of oil “acts as a mild and sure purgative”. In Indonesia, the bark of Aleurites moluccana (L.) Willd. is used to treat dysentery. In Malaysia, the seeds or the leaves are used to assuage headaches, heal ulcers and resolve swollen joints. The oil expressed from the seeds is used to treat sciatica. In the Philippines, the seeds are used to relieve the bowels of costiveness and treat cholera, while the leaves are used to treat rheumatism. The seeds of Aleurites moluccana (L.) Willd. are used to make soap and ointments. In India, the fruit is used to promote libido, invigorate health, expel worms from the intestines and to break fever. In Samoa, a dye extracted from the smoke of burned fruits is used to make tattoos. In the Sandwich Islands, the roots are used to dye native clothes. By the year 1890, the Sandwich Islands produced 10 000 gallons of oil from Aleurites moluccana (L.) Willd. which were exported to Europe to manufacture soap.

Pharmaceutical interest: An extract of Aleurites moluccana (L.) Willd. inhibits the growth of Staphylococcus aureus and Pseudomonas aeruginosa (Locher CP et al., 1995). It will be interesting to learn whether a more intensive study on this plant will disclose any molecules of therapeutic interest. References Lin TJ, et al. (1996) J of Toxicology — Clinical Toxicology 34(1): 87–92. Locher CP, et al. (1995) J Ethnopharmacol 49(1): 23–32. Satyanarayana P, et al. (2001) Fitoter 72(3): 304–306.

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Division MAGNOLIOPHYTA

Warning: This plant is toxic on account of complex phorbol diterpenoid esters, such as 13-O-myristyl-20-O-acetyl-12-deoxyphorbol, which are known to display Epstein-Barr Virus (EBV)-activating/tumor-promoting potency (Satyanarayana P et al., 2001). These irritating substances are most probably responsible for the counter-irritant and laxative property of the plant. Vomiting, abdominal pains and diarrhea were observed in school students who accidentally ingested the seeds of Aleurites fordii (Lin TJ et al., 1996). Aporosa arborea Muell.-Arg. [From Greek, aporos = difficult and from Latin, arbor = tree] Physical description: It is a tree which Synonymy: Leiocarpus arboreus grows to a height of 25 m in the lowBl., Leiocarpus arborescens Hassk., land rainforests of Thailand, the Malay Aporosa arborescens (Hassk.) Mull. ¨ Peninsula, Sumatra, West Java and BorArg. Daphniphyllum kingii Hook. f., neo. The bark is smooth and greyishBaccaurea forbesii Pax & K.Hoffm. brown. The stems are terete, smooth, Common names: Plueak khao and sparsely lenticelled. Leaves: sim(Thai). ple, spiral and stipulate.The stipules are caducous. The petiole is 3.4 cm–3 cm long and obscurely channeled above and curved at both ends. The blade is oblong-elliptic to obovate, 13.5 cm–35 cm × 4.5 cm–15 cm, and papery. The base is round to acute, and basal glands are absent. The margin is slightly undulate, the marginal glands are small. The apex is acuminate to cuspidate. The midrib at the base is sparsely puberulous above. The midrib and the nerves are sparsely puberulous underneath. A few disc-like glands are present along the margin.The nervations are slightly sunken above, and raised underneath. The blade shows 10–12 pairs of secondary nerves as well as scalariform tertiary nerves. The inflorescences develop from below the leaves or from the stems. The male flowers are 0.4 mm–0.8 mm long and yellow. The flower pedicels are indistinct. The calyx consists of 4 or 5 sepals which are obovate and 0.5 mm–0.8 mm long. The andrecium comprises of a pair of stamens which are slightly exserted and 0.3 mm–0.4 mm long. The anthers are 0.2 mm long.The female flowers are 2 mm–5 mm long and attached to 1.5 mm– 3 mm long pedicels. The calyx comprises of 5 sepals which are ovate, patent to slightly reflexed, and 0.6 mm–1 mm long. The ovary is globose, 3–4-locular and sparsely puberulous, and develops at the apex 3 stigmas of 0.7 mm– 1.5 mm length, which are bifid. The fruits are ellipsoid to globose, red-yellow and 1.7 cm × 1.2 cm–1.5 cm × 7 mm and show vestigial stigmas at the apex and vestigial sepals at the base. The fruits contain 1–3 seeds embedded in a red aril (Fig. 197).

Subclass Rosidae

339

Pharmaceutical interest: Uses: In Indonesia, Aporosa arborea Muell.-Arg. is used to invigorate and assuage articulation pains. In Malaysia, the roots are used to treat fever.

Antidiabetes properties: The pharmacological potential of Aporosa arborea Muell.-Arg. and of the genus Aporosa in general remains unexplored. Note that aqueous and alcoholic extracts of the root of Aporosa lindleyana (100 mg/kg) lower the levels of blood glucose of normal rats from 80.4 ± 2.7 mg% to 69.8±2.0 mg% and 82.6± 1.9 to 70.8 ± 3.2 mg%, respectively 3 hr after oral administration of the extracts (P